The method of obtaining-adamantylidene aliphatic and fatty-aromatic ketones

 

(57) Abstract:

The invention relates to derivatives of adamantane, namely to a new process for the preparation of carbonyl-containing adamantane derivatives of General formula

< / BR>
where R2= H; R1= H; R = CH3t-C4H9WITH6H5; R2= H; R1= CH3; R = CH3C2H5; R2= CH3; R1= CH3; R= i-C3H7which are intermediates for the synthesis of biologically active substances. The method consists in joining 1,3-dehydroalanine corresponding aliphatic ketones and fatty-aromatic series at a molar ratio of reactants is 1:(2-6), in an inert solvent or in the environment of the original ketone at a temperature of boiling ketones (56-120o(C) within 6-12 hours Method provides obtain the desired product with a yield of 60-80%.

The invention relates to the chemistry of adamantane derivatives, and in particular to a new process for the preparation of carbonyl-containing adamantane derivatives of General formula

< / BR>
where R2= H; R1= H; R = CH3t-C4H9WITH6H5; R2= H; R1= CH3; R = CH3WITH2H5; R2= CH3; R1=the STV.

A known method of producing substituted-1-acetone, consisting in the interaction adamantylidene acid chloride tiomila getting carboxylic adamantylidene acid and the subsequent processing of the Grignard reagent (from diethylmalonate and magnesium in the presence of cetarehhloristam carbon and ethyl alcohol), the hydrolysis and decarboxylation received adamantanemethylamine ether. [Lunn William Henoy, Szinai Stephen Slomo. The Patent In The UK. 1207954, publ. 7.10.70.]

The disadvantages of this method are primarily low yield of the final product (total yield in terms of the initial adamantane is 17-20%), with considerable loss of expensive reagents, a multi-stage synthesis. In the process of obtaining substituted-1-acetone is used diethylaniline, the substance is highly flammable, besides get such expensive compounds such as malonic ester and magnesium metal. The disadvantages of this method include the complexity and low adaptability of individual stages, particularly stage magyarkanizsa synthesis dangerous fire and placed high demands on the purity of the reagents.


The disadvantages of this method include the low yield of the final product (total yield in terms of the initial adamantane is 17-20%), the multistage synthesis and technological complexity.

Known also improved the above method in which the synthesis of substituted-1-acetone is carried out by acylation diethylmalonate ester acid chloride of 1-adamantanecarbonyl acid in the presence of solid sodium hydroxide and catalytic amounts of ethanol as promoting additives in the environment of toluene, followed by hydrolysis and decarboxylation adamantanemethylamine ether. [Prospects of organization of production anthropologie drug rimantadine in Russia. Moiseev, I. K., Klimushkin Y. N., Zimitchev A. C. , Stolin N. In. //Proc. Dokl. VII scientific conference of CIS countries "prospects of development of chemistry and the practical application of caged compounds", Volgograd, 1995, - S. 22-23.]

The disadvantages of this method are the relatively low yield of the final product (in terms of original adamantane 60%), also resulting in the loss of expensive raw materials, a multi-stage process.

Most blakley adamantane derivative (1-adamantanol) 2-chloropropanol environment 90-100% sulfuric acid at their molar ratio 1: (0,5-1,2): (7-15) and 0-30oIn the presence of a solvent, acetic acid, chloroform or methylene chloride at a mass ratio of adamantane derivative (1-adamantanol) and solvent of 1: (1.5 to 5). The output of substituted-1-ayatana depending on the molar ratio of the reactants and the concentration of sulfuric acid was 44-73% (in terms of original adamantane - 36-61%). [A. S. the USSR, 1512963, MCP 07 With 49/115, publ. 07.10.89.]

The disadvantages of this method is to conduct the process in a very acidic and relatively low yield of the final product.

The task of the invention is to develop technological molestating method of synthesis adamantylidene aliphatic and fatty-aromatic ketones, including isotrate (in particular the substituted-1-acetone and its homologues), proceeding with a high output source adamantane.

The technical result is to increase the output of the inventive compounds, as well as simplification of the mode of receipt.

The technical result is achieved in a new method of obtaining-adamantylidene aliphatic and fatty-aromatic ketones of General formula

< / BR>
where R2= H; R1= H; R = CH3t-C4H9WITH6N3H7,

which consists in joining 1,3-dehydroalanine ketones from a number of: acetone, methyl ethyl ketone, diethylketone, diisopropylate, methyltretbutylether, acetophenone at a molar ratio of reactants is 1:(2-6), in an inert solvent or in the environment of the original ketone at a temperature of boiling ketones 56-120oC for 6-12 hours.

The essence of the method is the reaction of joining 1,3-dehydroalanine ketones in their carbon atom:

< / BR>
The high nucleophilicity of 1,3-dehydroalanine allows you to get the products attach data ketones in high yields in a fairly mild conditions.

The advantage of this method is high (60-65% in terms of the initial adamantane) output, as well as the possibility of obtaining almost any homologues of this series, many of which are also intermediates for the synthesis of biologically active substances.

Found that the yield of the desired ketone is influenced by the following factors: the reaction temperature, duration of reaction, the structure of the original ketone. So, with the same conditions, the temperature increase interaction with the 50oWith up to 120oTo increase the output of products is on with ethyl ketone increases the yield from 40 to 72%. The effect of the structure of the original ketone in a yield of target products is the presence or absence of methylene carbon atoms, more active in the reactions of addition to 1,3-dehydroalanine compared to methyl. So, in the case of the interaction of methyl ethyl ketone with 1,3-dehydroalanine main product of the reaction (79oC, 12 hours) is a 3-substituted butanone-2, the product connection on methylene, and not a methyl group.

Thus, it is found that the optimal and technological condition of carrying out the reactions of addition of ketones to 1,3-dehydroalanine is in its implementation among the original ketone in a molar ratio of 1,3-dehydroalanine: ketone 1:2-6. Less excess has resulted in a slight decrease of the yield of the target products due to the poor solubility of 1,3-dehydroalanine in ketones, and also due to its possible homopolymerization. Further increase in the content of ketones did not affect the yield of target products was inappropriate. The optimal reaction temperature is the boiling point of ketones. Lowering the temperature leads to a strong increase in the duration of this interaction and the reduction of the yield of target products. The flow of this vorites such compounds, as pentane, hexane and other non-polar substances, as a reaction to their environment extremely difficult. Also prohibited the use of such solvents as alcohols, carboxylic acids, amines containing reactive towards dehydroalanine group.

The method is as follows.

To 2-6-fold molar excess of ketone is poured a solution of 1,3-dehydroalanine in boiling inert solvent, which is then removed from the reaction mixture by distillation. A mixture of 1,3-dehydroalanine and ketone are heated within 6-12 hours at the boiling point of the ketone, after which the excess ketone is distilled off. Regenerated ketone does not contain any impurities and is suitable for reuse in the same synthesis. Thus, in the industry you can organize recycling ketone with the addition of the calculated amount of fresh ketone. Synthesized-adamantylidene ketones after distillation of the original ketones are directed at the stage of cleaning. Output data products up to 90% (based on dehydroalanine).

The invention is illustrated by the following examples.

Example 1.

Synthesis of 1-(adamant-1-yl)acetone

< / BR>oWith, after which it stand 12 hours before the disappearance insoluble in ketone 1,3-DCA.

Upon completion of the reaction the excess acetone is removed by distillation, the residue is vacuum to remove unreacted 1,3-DCA, after which the product is distilled and receive of 3.42 g (0.018 mol, 60%) adamant-1-ilicitana representing a white crystalline substance. Properties ketone correspond to literature data.

Example 2.

Synthesis of 3-(adamant-1-yl) butanone-2

< / BR>
To 15 g (to 0.17 mol) of methyl ethyl ketone in an atmosphere of dry nitrogen at room temperature was added dropwise a solution of 4 g (0.03 mol) svezheosazhdennoi 1,3-DGA (the molar ratio of 1,3 DHA: ketone = 1:5) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, bringing the temperature of the reaction mixture up to the boiling point of the ketone to 79.6oWith, after which it stand 12 hours before the disappearance insoluble in ketone 1,3-DCA.

Upon completion of the reaction, excess ketone is removed by distillation, the residue is vacuum to remove unreacted 1,3-DCA, after which the product is distilled (BP. = 155oC./10 mm RT.CT.) and obtain 4.4 g (0,021 mol, 72%) of 3-(adamant-1- -1: 2896, 2844, 1704, 1455, 1416, 1352, 1064, 1028.

PMR-spectrum memorial plaques: 0,94 m (CH3, 3H); 1,46, 1,63, 1,98 3c (Ad, 15 NM); 2.1 m (CH3, 3H); 2,32 m (SN, N).

Found, %: C 81,04; N 11,72; O 7,24;

C15H26O

Calculated, %: C 81,02; N To 11.79; O 7,2.

Example 3.

Synthesis of 2-(adamant-1-yl) pentanone-3

< / BR>
To 11 g (0,128 mol) of diethylketone in an atmosphere of dry nitrogen at room temperature was added dropwise a solution of 4 g (0.03 mol) svezheosazhdennoi 1,3-DGA (the molar ratio of 1,3-DCA: ketone = 1:5) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, bringing the temperature of the reaction mixture up to the boiling point of the ketone to 79.6oWith, after which it stand 12 hours before the disappearance insoluble in ketone 1,3-DCA.

Upon completion of the reaction, excess ketone is removed by distillation, the residue is vacuum to remove unreacted 1,3-DCA, after which the product is distilled (BP = 129oC/4 mm RT.CT.) and obtain 4.5 g (0,020 mol, 69,2%) of 2-(adamant-1-yl) pentanone-3, representing a colorless transparent liquid, nD=1,5052.

The infrared spectrum , cm-1: 2904, 2844, 1712, 1456, 1120.

Found, %; 81,22; H a 12.03; O 6,75;

C16H28O

Calculated, %: C 81,29; N 11,94; O 6,77.

Example 4.

Synthesis of 2, anatoy temperature was added dropwise a solution of 4 g (0.03 mol) svezheosazhdennoi 1,3-DGA (the molar ratio of 1,3 DHA:ketone = 1:2) in 20 ml of absolute diethyl ether, then the solvent is distilled off, bringing the temperature of the reaction mixture up to the boiling point of the ketone, after which it can withstand 6 hours until the disappearance insoluble in ketone 1,3-DCA.

Upon completion of the reaction, excess ketone is removed by distillation, the residue is vacuum to remove unreacted 1,3-DCA, after which the product is distilled (BP. = 127oC/1 mm RT.CT.) and gain of 8.2 g (0,033 mol, 74,5%) of 2,4-dimethyl-4-(adamant-1-yl) pentanone-3, representing the white matter, crystalizes immediately after distillation, MP.=25oC.

The infrared spectrum , cm-1: 2936, 2880, 1732, 1484.

PMR-spectrum memorial plaques : 0,94-1.10 m (SN3, N); 1,42, 1,55, 1,95 3c (Ad, 15 NM); 2,48 m (SN, N).

Found, %: C 81,76; N 12,16; O BETWEEN 6.08;

C18H32O

Calculated, %: C 81,75; N 12,2; O 6,05.

Example 5.

Synthesis of 1-(adamant-1-yl) 3,3-dimethyl butanone-2

< / BR>
To 18 g (0.18 mol) of methyltretbutylether in an atmosphere of dry nitrogen at room temperature was added dropwise a solution of 4 g (0.03 mol) svezheosazhdennoi 1,3-DGA (the molar ratio of 1,3 DHA: ketone = 1:6) in 20 ml of absolute diethyl ether, after which the solvent is distilled off, bringing the temperature of the reaction mixture up to the boiling point of the ketone 114oWith, after which it vydergivayut distillation, the residue vacuum to remove unreacted 1,3-DCA, after which the product is distilled (BP. = 181-183oWith/8 mm RT. Art.) and gain of 2.93 g (0.012 mol, 42%) of 1-(adamant-1-yl) 3,3-dimethyl butanone-2.

The infrared spectrum , cm-1: 2952, 2884, 1748, 1496.

PMR-spectrum memorial plaques: 0,88 m (C(CH3)3, N); 1,62, 1,90, 2,08 3c (Ad, 15 NM); 2,22 m (CH2S(O) 2N).

Found, %: C 81,52; H 12,11; O 6,37;

WITH17H30ABOUT

Calculated, %: C 81,54; N 12,08; O 6,39.

Example 6.

Synthesis of (adamant-1-ylmethyl) phenylketone.

< / BR>
To 5 g (0,042 mol) of anhydrous acetophenone was added a solution of 2 g (0.015 mol) of 1,3-DGA (the molar ratio of 1,3 DHA:ketone = 1:2,5) in 20 ml of absolute ether. The resulting mixture is slowly distilled off ether and the reaction mixture is kept for 3 hours at 80-100oS, after which the excess acetophenone is distilled off in vacuum, the residue is maintained at 3 mm RT.article and 100oWith 1 hour and after recrystallization from ethanol 3,15 g (0,0124 mol, 84%) (adamant-1-ylmethyl)phenylketone. Properties ketone consistent with literature data. [ T. J. Broxton , Caper G., Deadfly L..W. the Electronic effect of bridgehead alkyl substituents: adaniantan-1-yl and bicycio [2,2,2] octan-1-yl. "J. Chem. Soc. Perkin Trans.", 1972, Part 2, No. 9, 1237-1240.]

Conclusions.

Developed technologically melastatin method of synthesis hell is Teal-1-acetone and its homologues), proceeding with a high output source adamantane.

The structure of the described compounds is confirmed by IR, PMR-spectra and elemental analysis.

Way to obtain-adamantylidene aliphatic and fatty-aromatic ketones of General formula

< / BR>
where R2= H; R1= H; R = CH3t-C4H9WITH6H5; R2= H; R1= CH3; R = CH3C2H5; R2= CH3; R1= CH3; R = i-C3H7,

using the adamantane derivative, characterized in that the method consists in joining the adamantane derivative of the corresponding carbonylic compounds, and as a derivative of adamantane using 1,3-dehydroalanine, and as carbonylic compounds ketones from a number of: acetone, methyl ethyl ketone, diethylketone, diisopropylate, methyltretbutylether, acetophenone and the process is carried out at a molar ratio of reactants is 1:2-6, respectively, in an inert solvent or in the environment of the original ketone at a temperature of boiling ketones 56-120oC for 6-12 hours

 

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