The method of obtaining adamant-1-ylamine and its derivatives

 

(57) Abstract:

The invention relates to the chemistry of adamantane derivatives, and in particular to a new method of obtaining amino adamantane General formula AdR, where R=NH2, NHBu-t,

< / BR>
< / BR>
< / BR>
which are biologically active substances and can find application in pharmacology and adamant-1-ylamine is the basis of the drug midantana". The technical result is to increase the output of the claimed compounds, the simplification of the process of acquisition and allocation of final products. The technical result is achieved in a new method of obtaining adamant-1-ylamine and its derivatives of the above formula by the interaction of the adamantane derivative with the corresponding amines or their derivatives, and the derivative of adamantane is used 1,3-dehydroalanine, and as amines or their derivatives - ammonia, tert.-butylamine, formamid, morpholine, piperidine, pyrrolidone-2, succinimide and phthalimide; the process is carried out at a molar ratio of reactants is 1:2 to 10, in the presence of catalytic amounts of epirate boron TRIFLUORIDE or in his absence, in an inert solvent, or in the source amines have had, or their production is the buy relates to the chemistry of adamantane derivatives, namely, to a new method of obtaining amino adamantane General formula AdP, where R=NH2, NHBu-t,

< / BR>
< / BR>
< / BR>
which are biologically active substances and can find application in pharmacology and adamant-1-ylamine is the basis of the drug midantana".

A method of obtaining adamant-1-ylamine and its derivatives from 1-bromoguanine and the corresponding amines (pyrrolidone-2-caprolactam and other ) in the presence of significant quantities of silver sulfate (Holland patent N 131489, A 61 K 27/00, C 07 C 87/40, publ. 17.05.71).

The disadvantages of this method are the use of expensive reagents (silver sulfate) and low (40%) the outputs of the reaction products.

A method of obtaining adamant-1-ylamine and its derivatives, consisting in the interaction of adamantylamine with the corresponding aldehydes with the intermediate Schiff bases, which are then restored with lithium aluminum hydride to the corresponding amines with a total yield of 50-60% (patent Norway N 113378, C 07 C 87/64, publ. 16.12.68).

The disadvantages of this method are its multi-stage, a limited number of the obtained compounds, the use of expensive and flammable aluminum hydride, the persons receiving adamant-1-ylamine and its derivatives, consisting in the introduction of alkyl radicals on the nitrogen atom adamant-1-ylamine using iodine Akilov by 12-16 hour boiling reagents in xylene followed by treatment with alkali. The output of 60-70% (patent Switzerland N 468341, C 07 C 87/40, publ. 31.-3.69).

The disadvantages of this method are the limitations of its application, using as starting reagent hard adamantylamine and iodine Akilov, which are not widely used in the industry.

A method of obtaining compounds of this formula, consisting in a long heated in a sealed ampoule mixture of adamantylamine, ethylene oxide and methanol for 20 h, followed by dehydration within 14 h of the formed intermediate product of concentrated sulfuric acid, leading to N-adamantylamine with a total yield of 60% (Synthesis of adamantane derivatives. Klimova N. Century , Arendaruk A. P., Baranov, M. A., Vasilchenko N. And., Marian M. I., Scaldino A. P.//Chem. The pharmacist. J., 1970, 4, N 11, 14-18).

The disadvantages of this method are its multi-stage, a limited number of the obtained compounds, high duration and low-tech process.

The closest is the way to receive the x derivative (n-butylamine, cyclohexylamine, adamantylamine, benzylamine, piperidine, morpholine, aniline, and others) in a sealed ampoule at 170-190oC, which leads to obtaining appropriate adamantylidene amines with outputs of 20-70% (Adamantane and its derivatives. XVIII. On the interaction of 1-bromoguanine with amines. Stepanov, F. N., Carpenters H. E.//Joh, 1969, 5, N 3, 537-541).

The disadvantages of this method are relatively low, the outputs of most products, low-tech (high temperature, conducting the reaction under pressure), because of the low reactivity of 1-bromantane.

The task of the invention is to develop a one-step method of obtaining adamant-1-ylamine and its derivatives in high yields.

The technical result is to increase the output of the claimed compounds, the simplification of the process of acquisition and allocation of final products.

The technical result is achieved in a new method of obtaining adamant-1-ylamine and its derivatives of General formula AdR, where R=NH2, NHBu-t, NHCH=O,

< / BR>
< / BR>
< / BR>
interaction adamantane derivative with the corresponding amines or their derivatives, and the derivative of adamantane is orfelin, piperidine, pyrrolidone-2, succinimide and phthalimide and the process is carried out at a molar ratio of reactants is 1:2-10, respectively, in the presence of catalytic amounts of epirate boron TRIFLUORIDE or in his absence, in an inert solvent or source amines, or derivatives thereof, at a temperature of 20-100oC for 1-6 h

The essence of the method is one-step reaction joining 1,3-dehydroalanine substances containing N-H, in the presence of a catalyst:

< / BR>
where R+NH2, NHBu-t, NHCH=O

< / BR>
< / BR>
< / BR>
The use of 1,3-dehydroalanine is unconventional, as it refers to the little-studied class of tight propellant. The high nucleophilicity of 1,3-dehydroalanine usually complicates the accession of amines, which have a high electron density at the reaction center on the nitrogen atom.

Used as a catalyst apirat boron TRIFLUORIDE is not only the share of the activation of 1,3-propranolol communication 1,3-dehydroalanine, but also to reduce the basicity of the nitrogen atom source amines and their derivatives by binding on the donor-acceptor mechanism of its lone-electron pairs, which leads to the surface is the ability of these reagents, consequently, the increase of the yield of the target adamant-1-ylamine and its derivatives.

The advantage of this method is the possibility of obtaining almost any derivatives adamant-1-ylamine, many of which have high biological activity, in one stage, with a good (60-99%) output as well as preparative ease of synthesis and ease of selection of the reaction products.

Conducted by the applicant's analysis of the prior art, including searching by the patent and scientific and technical information sources, and identify sources that contain information about the equivalents of the claimed invention, has allowed to establish that the applicant is not detected similar, characterized by signs, identical to all the essential features of the claimed invention, and determining from the list of unique prototype, as the most similar set of features analogue, has identified a set of essential towards perceived by the applicant to the technical result of the distinctive features in the claimed object set forth in the claims.

Therefore, the claimed invention meets the requirement of "novelty" by applicable law.

To check the initial search of the known solutions in order to identify signs, match the distinctive features of the prototype of the characteristics of the claimed invention, the results of which show that the claimed invention is not necessary for the expert in the obvious way from the prior art because the prior art defined by the applicant, not the influence provided the essential features of the claimed invention transformations to achieve a technical result.

Therefore, the claimed invention meets the requirement of "inventive step" by applicable law.

The method is as follows.

To the original amines or their derivatives prilisaetsa solution of 1,3-dehydroalanine in an inert solvent, after which the reaction mixture is added a catalytic amount of epirate boron TRIFLUORIDE (1-2 wt.%) and boil the reaction mass 5-6 hours the Process is carried out in an inert gas (nitrogen, argon) and in dried solvents (diethyl ether, hexane, heptane, and others). Possible reactions and among amines or their derivatives if they are liquid and have a boiling point in the region of 50-100oC. To suppress the possible adverse reactions homopolymers the ins or their derivatives. With less excess amines or derivatives thereof, a slight decrease of the yield of the target products, the use of an excess of more than ten-fold does not affect the yield of the reaction products and is impractical. It is noted that increasing the reaction temperature increases her speed and yield of the target products. Optimal temperature is 50-100oC. lowering the temperature to room noticeably slows down the reaction and increases the duration of the process and its increase above the 100oC reduces the yield of products of the reaction because of the formation of side-1,3-paludamentum and is impractical. In the case of low basicity of the original amine derivatives having a mobile hydrogen atom (for example, phthalimide), the use of a catalyst is not necessary, as these reagents possess sufficient reactivity with respect to 1,3-dehydroalanine.

Upon completion of the reaction, the catalyst is neutralized with an aqueous solution of alkali, extracted with ether, the organic layer washed with water, dried over CaCl2or Na2SO4the excess of the original amine and the solvent evaporated, the product is purified by distillation in vacuum or precipitated through the corresponding salt, for example the guy who comfort through a mixture solution of 1,3-dehydroalanine and catalytic amounts (1-2 wt.%) epirate boron TRIFLUORIDE within 1 h, then the reaction product emit the same way.

Example 1. Synthesis of adamant-1-ylamine

< / BR>
To saturated with dry ammonia to a solution of 0.5 g of epirate boron TRIFLUORIDE in 20 ml of absolute diethyl ether in the atmosphere Bartiromo ammonia was added dropwise at room temperature a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute ether. The bubbling of ammonia (15-20 ml/min) continue for 1 h at room temperature, after which the catalyst is washed with an aqueous solution of alkali, and then a small amount of water, the organic layer dried over CaCl2or Na2SO4the ether evaporated to dryness. Gain of 2.23 g (0,0145 mol, 99% of theoretical.) adamant-1-ylamine, AdNH2, TPL.= 181-182oC (lit. Tpl.=176-186oC).

Example 2. Synthesis of N-adamant-1-immortalia

< / BR>
To 10 g (0.12 mol) of dry research in the dry nitrogen atmosphere was added a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute hexane (molar ratio of 1,3 - DCA : morpholine 1:8), add 2-3 drops of epirate boron TRIFLUORIDE, the mixture boil for 4-5 h, the catalyst is neutralized with an aqueous solution of alkali, the water layer is extracted with ether, dried, the solvent and excess Moore. ) N-adamant-1-immortalia, TKip.=145oC/1 mm RT. Art., TPL=58-59oC (lit Tpl.= 62oC).

Example 2. Synthesis of N-adamant-1-ipipeline

< / BR>
To 10 g (0,117 mol) of dry piperidine in dry nitrogen atmosphere was added a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute hexane (molar ratio of 1,3 - DCA : piperidine 1:8), add 2-3 drops of epirate boron TRIFLUORIDE, the mixture boil for 5-6 h, the catalyst is neutralized with an aqueous solution of alkali, the water layer is extracted with ether. The organic layer is dried, the solvent and excess piperidine is distilled off in a water jet vacuum pump, the product is distilled in a vacuum. Obtain 2.6 g(0.012 mol, 76% of theoretical.) N-adamant-1-ipipeline, TKip.=155oC/2 mm RT. Art., Tpl.=68oC (lit. Tpl.=68oC).

Example 4. Synthesis of N-adamant-1-ipipeline

< / BR>
A mixture of 12 g (0.15 mol) of dry piperidine, 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine (the molar ratio of 1,3 - DCA : piperidine 1: 10) and 2-3 drops of epirate boron TRIFLUORIDE is heated at a temperature of 100oC in dry nitrogen atmosphere for 4 hours At the end of the reaction the catalyst is neutralized with an aqueous solution of alkali, the water layer twice EXT pump, the product is distilled in a vacuum. Get 2.66 g (0,013 mol, 79% of theory.) N-adamant-1-ipipeline, TKip.= 155-156oC/2 mm RT. Art., Tpl.=67,5oC (lit. Npl.=68oC).

Example 5. Synthesis of N-adamant-1-ID-2-pyrrolidone

< / BR>
To 5 g (0.06 mol) of dry pyrrolidone-2 in dry nitrogen atmosphere was added a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute hexane (molar ratio of 1,3 - DCA : pyrrolidone-2 1: 8), add 2-3 drops of epirate boron TRIFLUORIDE, the mixture boil for 4-5 h, the catalyst is neutralized with an aqueous solution of alkali, the aqueous layer was twice extracted with ether, dried, the solvent is distilled off in a water jet vacuum pump, the excess of pyrrolidone-2 is distilled off in a vacuum and then distilled product. Gain of 2.45 g (74% of theory.) N-adamant-1-yl-2-pyrrolidone, TKip.=165oC/4 mm RT. Art., Tpl.=97oC (lit. Tpl.=97-100oC).

Example 6. Synthesis of N-adamant-1-iltram.-of butylamine

< / BR>
To 10 g (0.14 mol) of dry tert.-of butylamine in an atmosphere of dry nitrogen was added a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute hexane (molar ratio of 1,3 - DCA : tert.-butylamine 1: 9), add 2 to 3 drops of epirate boron TRIFLUORIDE, actuarial and excess tert.-the butylamine is distilled off in a water jet vacuum pump, the product is distilled in a vacuum. Obtain 1.86 g (0,009 mol, of 60.5% of theory.) N-adamant-1-yl-tert.-of butylamine, TKip.=152oC/3 mm RT. Art., Tpl.=65-66oC (lit. Tpl.=65oC).

Example 7. Synthesis of N-adamant-1-Informatica

< / BR>
To 5 g (0,111 mol, 7-fold excess) of dry formamide in a dry nitrogen atmosphere was added a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute tetrahydrofuran (the molar ratio of 1,3 - DCA : formamid 1:8), add 2-3 drops of epirate boron TRIFLUORIDE. The mixture is boiled for 3-4 hours, the catalyst is neutralized with an aqueous solution of alkali, the water layer is extracted with ether, dried. The solvent is distilled off, the excess formamide is removed in vacuum, the product is distilled. Gain of 1.97 g (to 0.011 mol, 76% of theoretical.) N-adamant-1-immortalia, Tpl.=146-148oC (lit. Tpl.=146oC).

Example 8. Synthesis of N-adamant-1-isucceed

< / BR>
To a mixture of 5 g (0,051 mol) of succinimide and 10 ml of absolute diethyl ether in a dry nitrogen atmosphere was added a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute ether (molar ratio of 1.3 LGA : succinimide 1:3,5), add 2-3 drops of epirate boron TRIFLUORIDE, the mixture is heated gradually driving rosalea excess of the original succinimide in the form of a salt, the aqueous layer was extracted with ether, dried. The solvent is distilled off in a water jet vacuum pump, the product is distilled in a vacuum. Get 2,82 g (0.012 mol, 81% of theoretical.) N-adaman-1 isucceed, TKip.=169-171oC/3 mm RT. Art.

Example 9. Synthesis of N-adamant-1-italkid

< / BR>
To a mixture of 5 g (0,034 mol) phthalimide and 10 ml of absolute diethyl ether in a dry nitrogen atmosphere was added a solution of 2 g (0.015 mol) svezheosazhdennoi 1,3-dehydroalanine in 20 ml of absolute ether (molar ratio of 1,3 - DCA : phthalimid 1:2), the mixture is heated gradually fending off the solvent, 60oC and boiled for 3 h, after which the excess of the original phthalimide remove the alkali solution, the aqueous layer was extracted with ether, dried, the solvent is distilled off in a water jet vacuum pump. Get to 3.73 g (0,013 mol, 85% of theoretical.) N-adamant-1-Italija, Tpl.=136oC (lit. Tpl.=140oC).

Use the reactions of addition of amines and their derivatives by 1,3-dehydroalanine is a convenient one-step method of obtaining a variety of amino adamantane with high yields (70-99%).

Thus, the above data confirm that the implementation of the use of the claimed invention, shadowmachine for use in various industries;

for the claimed invention in the form as it is described in the independent clause following claims, confirmed the possibility of its implementation using the above described in the application or known before the priority date tools and techniques;

the tool embodying the claimed invention, it is able to achieve a technical result.

Therefore, the claimed invention meets the requirement of "industrial applicability".

The method of obtaining adamant-1-ylamine and its derivatives of General formula

AdR,

where R = NH2, -NHBu-t, -NHCH=O,

< / BR>
< / BR>
< / BR>
interaction adamantane derivative with a corresponding amine or its derivatives, characterized in that as adamantane derivative use 1,3-dehydroalanine, and as an amine or its derivative ammonia, tert. butylamine, formamid, morpholine, piperidine, pyrrolidone-2, succinimide or phthalimide and the process is carried out at a molar ratio of reactants is 1 : 2 to 10, respectively, in the presence of catalytic amounts of epirate boron TRIFLUORIDE or its absence, in an inert solvent or in the environment of the original amine or its PR

 

Same patents:
The invention relates to chemical technology, more specifically, to improved method of separation of acetylene from waste gases for 1,4-butandiol (1,4-BID) on the basis of acetylene and formaldehyde

The invention relates to new 8-carbonylation 2-aminotetraline, their enantiomers and salts, processes for their preparation, pharmaceutical preparations on their basis and use of such compounds in therapy

The invention relates to methods of obtaining salt corrosion inhibitor

The invention relates to the production of stabilizers on the basis of substituted amines and can be used to obtain rubber, vulcanization agents and other polymeric materials

The invention relates to a vapor-phase process for the production diarization amines by the catalytic condensation of the corresponding primary amines, specifically, diphenylamine (DFA) of aniline

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing aliphatic amines by addition reaction of ammonia to (C2-C8)-alkenes, for example, to isobutylene in gaseous phase and reaction is catalyzed by heterogeneous, preferably zeolite catalyst. Process is carried out in system comprising two sections - separating and reaction that are interrelated and interdependent and one cooling zone working under the same pressure from 2 to 8 MPa. Liquid mixture of ammonia and alkene is fed to upper part of separating section fitted with dephlegmator and then mixture is fed to reaction section containing catalyst, for example, zeolite catalyst of type ZSM-5 wherein alkene reacts with ammonia partially and forms amine. Temperature in reaction section is maintained usually from 220oC to 320oC and the molar ratio of ammonia to alkene at inlet to reaction section is from 1.5 to 20 usually. Then reaction mixture removing reaction section is cooled in cooling zone to temperature about the condensation point by heat-exchange with mixture that is recovered for repeated utilization from separating section to reaction section. Cooled reaction mixture is recovered to separating section fitted with built in packing for intensification of mutual contact of countercurrent of liquid and gaseous phases wherein the amine concentrate is separated from reaction mixture and removed from heated vat of separating section. Indicated concentrate is purified additionally and unreacted mixture of alkenes and ammonia in common with fresh parent compounds is recovered for repeated processing in gaseous form from condenser of this section to reaction section. Method provides reducing energy consumptions due to reducing heat consumptions and pressure.

EFFECT: improved preparing method.

12 cl, 1 dwg, 2 ex

FIELD: organic chemistry.

SUBSTANCE: target products is produced by ethylene diamine transamination. Reaction is carried out at 135-180°C at pressure of 5-40 MPa in presence of hydrogen and catalyst particles containing 26-65 wt.% of metallic nickel on porous carrier.

EFFECT: high ethylene diamine conversion ratio and high selectivity in relate to target acyclic polyethylene polyamines under advantageous reaction conditions.

10 cl, 2 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: proposed invention pertains to organic chemistry, more specifically to the method of producing N,N-dimethyl-3-phenyl-2-propyne-1-amine. The method involves reacting phenylacetylene with excess bisamine in the presence of a vanadyl acetylacetonate catalyst (VO(acac)2) in an argon atmosphere at 85°C temperature and atmospheric pressure for a period of 4-8 hours. N,N-dimethyl-3-phenyl-2-propyne-1-amine output is 84-98%.

EFFECT: invention can be used in thin organic synthesis, particularly for making not easily accessible polycyclic compounds, as well as in synthesis of biologically active substances.

1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing N,N,N,N-tetramethylalkadiynediamines, which can be used in fine organic synthesis, particularly for producing not easily accessible polycyclic compounds, as well as in synthesis of biologically active substances. Desired compounds are obtained from reacting diacetylene alkanes with excess N,N,N,N-tetramethylmethane diamine in the presence of a vanadyl acetylacetonate (VO(acac)2) catalyst, in molar ratio diacetylene alkane: N,N,N,N-tetramethylmethane diamine: VO(acac)2 = 10:(25-35):(0.2-0.4) in an argon atmosphere at temperature ranging from 70 to 100°C, mostly at 80°C, and atmospheric pressure for 4 to 8 hours.

EFFECT: method considerably simplifies synthesis schematic due to use of accessible initial reagents and significantly increases output of desired products, and allows for obtaining new and known compounds.

1 cl, 3 dwg, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing N1,N1,N4,N4-tetramethyl-2-butyne-1,4-diamine, which is used in synthesis of polycyclic compounds, as well as in synthesis of biologically active substances. The method involves reaction of N,N,N,N-tetramethylmethane-diamine with excess gaseous acetylene in the presence of a VO(acac)2 catalyst, taken in molar ratio of N,N,N,N-tetramethylmethane-diamine: (VO(acac)2) = 10 : (0.3-0.5), preferably 10:0.4, at temperature 65-75°C and atmospheric pressure for 1-3 hours.

EFFECT: method increases output of the desired product.

1 cl, 3 dwg, 1 tbl, 1 ex

FIELD: chemistry.

SUBSTANCE: method involves reaction of bisamine with 3-fold excess acetylene in the presence of a vanadyl acetylacetonate (VO(acac)2) catalyst in an argon atmosphere at temperature 70°C and atmospheric pressure for 3 hours, followed by addition of diisobutylaluminium hydride and stirring the reaction mixture for 4-6 hours at room temperature. The method enables to obtain N1,N1,N4,N4-tetramethyl-2-butene-1,4-diamine from available reagents with quantitative output of (82-97%).

EFFECT: high output of end product.

1 tbl, 3 dwg, 1 ex

Purification method // 2444511

FIELD: chemistry.

SUBSTANCE: present invention relates to versions of a method of purifying terbinafine from nonmetallic impurities, primarily a substance A of formula

, as well as to use of said methods to obtain purified terbinafine. One of the versions of the method involves molecular distillation of crude terbinafine in form of a free base and extraction the obtained purified terbinafine in form of a free base or acid-addition salt (method A). In another version (method B), crude terbinafine in form a free base undergoes molecular distillation combined with formation of a salt of the obtained product with simultaneous deposition of a purified trans-isomer, and the obtained highly pure terbinafine is extracted in form of a free base or acid addition salt.

EFFECT: method enables to obtain terbinafine containing less than approximately 5 ppm of substance A.

13 cl, 2 dwg, 6 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing at least one product from acrolein and acrylic acid via partial oxidation of propylene, where a) purified propane is converted at the first reaction step in the presence and/or absence of molecular oxygen, at least one dehydrogenation from a group comprising homogeneous dehydrogenation, heterogeneous catalytic dehydrogenation, homogeneous oxydehydrogenation and heterogeneous catalytic oxydehydrogenation, wherein a gaseous mixture 1 is obtained, which contains unconverted propane and the formed propylene, and b) optional separation from the total amount or partial amount of the gaseous mixture 1 of a partial amount of components other than propane and propylene contained therein, e.g., hydrogen, carbon monoxide, water vapour and/or optional conversion thereof to other compounds, e.g., water and carbon dioxide, and where a gaseous mixture 1' is obtained, which contains propane and propylene, and on at least one of the following reaction steps, c) the gaseous mixture 1 or gaseous mixture 1' or a mixture from the formed gaseous mixture 1' and the remaining gaseous mixture 1 as a component of a gaseous mixture 2 are subjected to heterogeneous catalytic gas-phase partial oxidation of propylene contained in gaseous mixture 1 and/or gaseous mixture 1', wherein a gaseous mixture 3 is obtained, which contains at least one product, d) on at least one separation step, the product is separated from gaseous mixture 3 and from the remaining residual gas, at least propane is returned to the first reaction step, where purified propane is obtained from crude propane which contains ≥90 wt % propane, ≤99 wt % propane and propylene, ≥100 ppm hydrocarbons, having 2 carbon atoms, and ≥100 ppm hydrocarbons, having 4 carbon atoms, under the condition that crude propane is fed into the fractionation column and purified propane is obtained higher than the feeding point under the condition that content of hydrocarbons having 2 carbon atoms, in wt %, in terms of the contained propane, in the purified propane is more than 100% of the corresponding content in crude propane and content of hydrocarbons having 4 carbon atoms, in wt %, in terms of content of propane, in the purified propane is at most 50% of the corresponding content in crude propane.

EFFECT: method enables to cut design expenses owing to no separation of C2-hydrocarbons during distillation.

48 cl, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to an improved method of producing N1,N1,N4,N4-tetramethyl-2-butyne-1,4-diamine, which can be used in fine organic synthesis, particularly for producing scarce polycyclic compounds, as well as in synthesis of biologically active substances. The method involves reaction of bisamine with excess gaseous acetylene in the presence of a VO(acac)2 catalyst at temperature 65-75°C and atmospheric pressure for 1-3 hours.

EFFECT: method enables to obtain N1,N1,N4,N4-tetramethyl-2-butyne-1,4-diamine from available reactants with quantitative output of 76-98%.

1 tbl, 3 dwg, 1 ex

FIELD: chemistry.

SUBSTANCE: invention relates to a method of producing novel N-alkyl-3-methyl-4-nitrosoanilines of formula where R=i-Pr, cyclohexyl. The compounds can be used as modifiers and stabilisers of rubber mixtures and as starting compounds for synthesis of N-substituted n-phenylene diamines, which are used to produce a wide range of azo dyes and in colour photography. The method involves cyclocondensation of acetone and the corresponding amine with a product of nitrosation of 4,4-dimethoxybutan-2-one, which is first held in aqueous hydrochloric acid solution.

EFFECT: improved method.

2 ex

FIELD: organic chemistry, medicine, pharmacy.

SUBSTANCE: invention describes compound of the formula (I):

as a free form or salt wherein Ar means group of the formula (II):

wherein R1 means hydrogen atom or hydroxy-group; R2 and R3 each means independently of one another hydrogen atom or (C1-C4)-alkyl; R4, R5, R6 and R7 each means independently of one another hydrogen atom, (C1-C4)-alkoxy-group, (C1-C4)-alkyl or (C1-C4)-alkyl substituted with (C1-C4)-alkoxy-group; or R5 and R6 in common with carbon atoms to which they are joined mean 6-membered cycloaliphatic ring or 6-membered heterocyclic ring comprising two oxygen atoms; R8 means -NHR13 wherein R13 means hydrogen atom, (C1-C4)-alkyl or -COR14 wherein R14 means hydrogen atom; or R13 means -SO2R17 wherein R17 means (C1-C4)-alkyl; R9 means hydrogen atom; or R8 means -NHR18 wherein -NHR18 and R9 in common with carbon atoms to which they are joined mean 6-membered heterocycle; R10 means -OH; X means (C1-C4)-alkyl; Y means carbon atom; n = 1 or 2; p = 1; q = 1; r = 0 or 1. Also, invention describes pharmaceutical composition based on compound of the formula (I), a method for preparing compound of the formula (I) and intermediate compound that is used in the method for preparing. Compounds elicit the positive stimulating effect of β2-adrenoceptor.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

13 cl, 3 tbl, 35 ex

Up!