GB531208A - Manufacture of basic esters - Google Patents

Abstract

531,208. Basic esters. GROVES, W. W. (I. G. Farbenindustrie Akt.-Ges.). July 12, 1939, No. 20307. [Class 2 (iii)] Basic esters of the general formula where R, and R 2 are aryl groups, R 3 is a basically substituted alkyl radical and R 4 is an alkyl or aralkyl radical, are prepared by reacting a nitrile of the general formula <SP>R</SP>1# CHÀCN with an alkyl halide containing R 2 # a tertiary amino group as substituent in the presence of an agent for splitting off hydrogen halide, and transforming the tertiary nitrile thus obtained into the corresponding ester. The compounds are stated to be excellent spasmolylica. In examplas (1) Sodium amide is added to diphenylacetonitrile in benzene solution and then to the reaction product there is further added a benzene solution of piperidineethyl chloride. On the addition of acid there separates the hydrochloride of diphenylpiperidino-ethylacetic acid nitrile which is converted to the base by means of alkali. This compound is then heated with sulphuric acid in an oil bath to 145‹-150‹ O. to effect hydrolysis of the nitrile. Ethyl alcohol is then added and after the esterification there is obtained the ethyl ester of diphenylpiperidino-ethylacetic acid. Instead of piperidino-ethyl chloride there may be used diethylaminoethyl chloride to give dipbenylethylaminoethylacetic acid ethyl ester. (2) The saponification product of diphenylpiperidino-ethyl-acetonitrile prepared as in example (1) are esterified with isopropyl alcohol to give the corresponding isopropyl ester.