SU168675A1 - METHOD OF OBTAINING NITRILE a, a-DIPHENYL-p-METHYL-y- (N-MORPHOLYL) OIL ACID ftXWr4Wjif * || KP,> & F) T!. ^ 'A - Google Patents

Description

The invention relates to the field of production of intermediate products for the synthesis of anesthetic preparations.

Upon receipt of the nitrile a, a-diphenyl-p-methyl-Y- (N-morpholyl) butyric acid, small yields of the product (up to 20 ° / o) and a large amount of by-products are obtained by known methods.

In order to increase the yield, it has been proposed to prepare nitrile ", a-diphenyl-p-methyl-y- (K-morpholyl) butyric acid by reacting acetal a-methyl- | 3, | 3-diphenyl- | 3-cyanopropionic aldehyde with morpholine or N- formylmorpholine and formic acid in the presence of a mineral acid, for example hydrochloric. The use of only a-methylr for the reaction, (3-diphenyl-p-cyanopropionic aldehyde does not give a positive result.

If acetaldehyde is used as a raw material, it is recommended to add mineral acid to the reaction mass to speed up its hydrolysis.

Example 1. In a three-necked 500 ml flask equipped with a stirrer, a thermometer, a reflux condenser and a dropping funnel, 139.5 g (1.6 mol) of morpholine was charged and 92.5 g (15 1.75 mol} 880 / o-formic acid. The flask is cooled with water, maintaining the temperature 50-

60 ° C. After the addition, the mass is heated on a petrolatum bath to 112-114 ° C, and then boiled for one hour under reflux. The reaction mass, containing formylmorpholine, is cooled and 64.7 g (0.20 mol of acetal a-methyl-p, p-diphenyl-p-cyanpropionic aldehyde, 21 g (0.4 mol) of 888 / o-th formic acid and 6.8 g (0.067 mol} of concentrated hydrochloric acid. The mixture is heated to boiling and boiled for 6 hours, after which the mixture of ethyl formate, water and formic acid is distilled from the reaction mass. is about 112 ° C and only towards the end of the distillation begins to rise to 150-155 ° C.

A total of 54 ml of the low boiling fraction was distilled off.

The reaction mass is maintained for 6 hours at a temperature of 150-155 ° C. At the end of the exposure, the solution is cooled and 13.6 g (0.134 mol} of concentrated hydrochloric acid is added at a temperature, the flask is cooled with water. A precipitate of nitrile hydrochloride is deposited. To the mass, 100 ml of benzene are added, the precipitate is filtered, it is recrystallized from water. 57.0 g of nitrile hydrochloride a are obtained, a-diphets with mp 196-198 ° C, which is from the theoretical value, based on the starting acetal.

Example 2. In a three-neck flask, with a capacity of 100 ml, equipped with a stirrer, thermometer and reflux condenser, load 9.96 g (0.03 mol) acetal a-methyl-p, p-diphenyl (3-cyano-propionic aldehyde, 27.63 ml (0.24 mol) formylmorpholine, 2.55 ml (0.66 mol) of 880 / o-formic acid and 1 ml of concentrated hydrochloric acid.

The mixture is heated to boiling (103-106 ° C) and rolled for 6 hours, after which water, ethyl formate and formic acid are distilled off from the reaction mass. At the end of the distillation, the mixture is incubated for 6 hours at a temperature of 155 ° C. After cooling, 2 g of concentrated hydrochloric acid and 10 g of benzene are added. Filtered wasp, nitrile a, a-a-diphenyl-p-methyl-y- (α-morpholyl) butyric acid doc hydrochloride is recrystallized from water. Yield 7.7 g, which is 80 ° / o of theoretical, based on the starting acetal. T. pl. 196-198 ° C.

Subject invention

The method of obtaining a and a-diphenyl-methyl-y- (M-morpholyl) butyric acid nitrile, characterized in that, in order to increase the yield, a-methyl-p, p-dipheiyl-p-cyaipropionic aldehyde acetal is reacted with morpholine or N-formylmorpholine and formic acid in the presence of a mineral acid, for example, salt.

,

..:; g ...,