Catalyst to obtain 1-alkoxy-2,3 - diphenylethylamine

 

(57) Abstract:

The invention relates to the field of catalysts, in particular a catalyst to obtain 1-alkoxy-2,3-diphenylethylamine. The resulting catalyst consists of douglasthe cobalt, an activator of triphenylphosphine and alkoxysilylated as a reductant, taken in a molar ratio 1: (1,5-2,5): (2-6) respectively. The advantage of the catalyst is its accessibility. table 1.

The invention relates to the field of catalysts, in particular catalysts for production of 1-alkoxy-2,3-diphenylethylamine (1), which can find application in organic and ORGANOMETALLIC synthesis.

Known two-component catalyst /U. M. Dzhemilev, A. G. Ibragimov, I. R. Ramazanov, L. M. Khalilov. Lumastrobe - a new class alyuminiiorganicheskikh compounds. WPI. An. Ser. chem. , 1997, 12, 2269-2270 /to obtain 1-ethyl-2,3-diphenylethylamine consisting of titanzincoated Cf2iCl2and ethylaminoethanol (EtAlCl2).

The disadvantage is the inaccessibility of one of the catalyst components (Cp2TiCl2), which in the country is not possible and is synthesized in two SUB>4.

Known catalyst /U. M. Dzhemilev, A. G. Ibragimov, I. R. Ramazanov, R. C. Kunakova, L. M. Khalilov, A. H. Islamgulova, A. H. Sharipova. The way the joint production of 1-(alkoxy)-2,3,4,5-tetraalkyl(aryl)-almacenamiento and 1-(alkoxy)-2,3-dialkyl(aryl)aromaticivorans. Patent RU 2130024 C1, 10.05.1999/ for the joint production of 1-alkoxy-2,3-diphenylethylamine (1) and 1-alkoxy-2,3,4,5-tetraphenylcyclopentadienone consisting of zirconatetitanate Cf2Zr12.

The disadvantage is the inaccessibility of the catalyst Cp2ZrCl2who in the country is produced and synthesized on the basis of pyrophoric Na, easily polymerizing Dicyclopentadiene WITH5H6and hygroscopic ZrCl4in two stages. In addition, a known catalyst leads to the formation of hardly separated a mixture of 1-alkoxy-2,3-diphenylethylamine (1) and 1-alkoxy-2,3,4,5-tetraphenylcyclopentadienone.

A new catalyst to obtain 1-alkoxy-2,3-diphenylethylamine (1).

The proposed catalyst is available douglasthe cobalt (So2), an activator of triphenylphosphine (PH3R) and alkoxysilylated RO-lCl32to cobalt in low-valence state, which complexesa RH3R with the formation of the active complex.

In the presence of the specified catalyst formed 1-alkoxy-2,3-diphenylethylamine (1) outputs 56 -77%. The reaction is carried out in an inert atmosphere by the interaction of diphenylacetylene (Ph--Ph) alkoxysilylated RO-AlCl2where R= Et, n-Bu, n-Neh and magnesium (powder), taken in a molar ratio Ph--Ph:RO-AlCl2= 10:14:12, at a temperature of 21-22oWith in tetrahydrofuran (THF) for 12 hours according to the scheme:

< / BR>
[From] = So2+RH3R+RO-AS2; R= Et, n-Bu n-Hex

The amount of catalyst required for the reaction 3-6% compared to the original diphenylacetylene.

Differences between the proposed catalyst known from the following: components of the proposed catalyst are manufactured in the country duplissy cobalt (CoCl2), available activator PH3R and restorer RO-A1C12(R= Et, n-Bu n-Hex).

The invention is illustrated by examples

EXAMPLE 1. The preparation of the catalyst. In a glass reactor with a volume of ~ 50 ml installed on a magnetic stirrer, an argon atmosphere was placed 0.5 mmol CoCl2, 1.0 mmol of RHproduce an active catalyst.

EXAMPLE 2. Cycloalumination of diphenylacetylene. The resulting catalyst was added when -5oTo the reaction mass, consisting of 10 mmol of diphenylacetylene, 12 mmol of magnesium powder and 14 mmol EtO-AlCl2in 10 ml of dry THF, stirred for 12 hours at a temperature of 21-22oC. Receive 1 ethoxy-2,3-diphenylacetamide with the release of 69%. The yield of the target product (1) is determined using GC by analysis of the hydrolysis products. Products lateralize confirm receipt of the target product (1). When lateralize 1 ethoxy-2,3-diphenylethylamine (1) is formed CIS-1,2-dideuterio-1,2-diphenylethylene (2) according to the scheme:

< / BR>
An NMR spectrum13With (, memorial plaques , Me4Si6D6) CIS-1,2-dideuterio-1,2-diphenylethylene (2): 130,12 (1I , JC-D= 23.1 Hz), 137,04 (2), 128,15 (3), 128,79 (4), 127,11 (5).

Other examples of the invention, shown in the table.

The catalyst was prepared in THF at a temperature of -5oWith the response of cycloalumination was carried out at room temperature (21-22oC) within 12 hours

Catalyst to obtain 1-alkoxy-2,3-diphenylethylamine, characterized in that it is obtained by the interaction douglasthe cobalt l2the act is as reductant in the following molar ratio of the components: l2: Ph3R: RO-AlCl2= 1: (1,5-2,5): (2-6).

 

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