SU856377A3 - Method of preparing cis-bicyclooctylamines - Google Patents

Description

t

The present invention relates to an improved method for the preparation of 2-phenylbiciyl octoanes Formula 1, possessing physiological activity.

It is known that compounds of the formula

(Y

t

H

TC & R and C alkyl;

Ar is a phenyl group, which may contain two halogen atoms as substitutes, is obtained by reduction of the corresponding nitrile, followed by alkylation of the obtained khilin to the desired product successively in two stages f13.

The disadvantage of this method is the multistage process.

The aim of the invention is to simplify the process.

This goal is achieved in that the compounds of the formula

Ci-NR K

.C-N B-i-M P

Where

"A hydrogen atom or taken together form a single bond

 X is a hydrogen, bromine or chlorine atom catalytically derived from hydrogen at P + 0.

Example 1 Cys-2- (3,4-di10 chlorophenyl) -3-N, N-dimethylaminomethyl-bicenclic (2,2,2) -octane.

Platinum oxide (106.8 mg) is hydrogenated at room temperature in isopropanol (3 ml). Absorption

t5, hydrogen after 20 minutes is

21.8 ml (according to the theory 21.15 ml). 2- (3,4-Dichlorophenyl) -bicyclo- (2,2,2) -oxy-3-N, N-dimethylaminoylidene (189 mg; in isopropanol (2 ml) is added to

20 hydrogenating mixture for 45 minutes Hydrogen uptake is 1418 ml Spo theory (13.7 ml). The filter is filtered, after evaporation of the filtrate, an oil is obtained (yield

25 15.3mg, 81%). This oil is dissolved in 5N. hydrochloric acid and extracted with ether. The ether extract is washed with water, dried over magnesium sulphate, after evaporation an oil is obtained (yield 70.7 mg, 37%), the neutral components thus obtained are removed as a result of the reaction. The hydrochloric acid extract is neutralized with 5 ml of NaOH and extracted with ether. The ether is washed with water, dried over anhydrous magnesium sulphate, after evaporation the desired product is obtained in the form of an oil (yield 72.9 mg, 38.5% Proof of structure obtained by NMR and GLC. These analytical methods showed that the reaction product represents is a very pure cis substance, (98%) with only small amounts of 2% trans substance present as an impurity.

Example 2 Cys-2- (3,4-di. Chlorophenyl; -3-N, N-dimethylaminomethyl methylcylo- (2,2,2) -octane.

Platinum oxide (108 mg) is hydrogenated at atmospheric pressure in benzene (3 ml) at room temperature for 1 h. Then benzene (25 ml) is added and the mixture is heated under reflux with a Dean-Stark nozzle. After 2 h, catalyst three washed with ethanol (30 ml), ethanol (3 ml) was added to the catalyst and hydrogenated with 1 h 2-i3,4-dichlorophenyl) -bicyclo- (2,2,2) -oct-2-en-3-N, N-dimethylaminoylidene-3 (225 mg) in ethanol (2 ml is introduced into the apparatus and the mixture is hydrogenated; after 3 h, the absorption of hydrogen is 33.1 ml (according to theory 34.1 ml). The catalyst is filtered, after evaporation of the filtrate an oil remains, which is dissolved in 5 H.HCl and extracted with ether. The ether extract is washed and after evaporation an oil is obtained, yield 101.5 mg). The aqueous sulphate extracts are treated with alkali (5 ml of NaOH) and extracted with ether. The ether extracts are washed, dried, and after evaporation, half an oil is obtained (yield 90 mg, 38.3%).

According to NMR, GLC, mass spectroscopy, this oil is a mixture of 86% cis and 14% transisomers.

Claims (1)

1. A process for the preparation of cis-bicyclo octylamines of formula 1: No n  alkyl Me and Where And g is a phenyl group, which may contain as substituents two halogen atoms using a reduction reaction characterized in that, in order to simplify the process, a compound of the formula I .  l% where Р „and R; - a hydrogen atom or taken together form a simple bond X - a hydrogen atom, bromine or chlorine, subjected to catalytic reduction at P + O / j. Information officers taken into account during the examination 1. For the application of FRG 2619617, cl. C 07 C 87/40, published on 18.11.76 (prototype).