Patent GB-536211-A (GB)
Title: Manufacture of alkamine esters of di-alicyclic- or aryl-alicyclic-fatty acids
Filed: 1939-08-01
Abstract: 536,211. Esters ; amides. SOC. OF CHEMICAL INDUSTRY IN BASLE. Aug. 1, 1939, No. 22279 and 22280. Convention dates, Aug. 5, 1938 and June 20, 1939. [Class 2 (iii)] Alkamine esters of di-alicyclic- or arylalicyclic-fatty acids are prepared by the catalytic hydrogenation of the corresponding diphenyl-fatty acid esters. The products, which may be converted into their quaternary salts, possess therapeutic properties. According to the examples, diphenylacetic acid 2-diethylaminoethanol ester is hydrogenated in presence of activated platinum prepared by reducing platinic oxide and the resulting mixture of the diethylaminoethanol esters of dicyclohexylacetic acid and phenylcyclohexylacetic acid separated ; the former may be converted into its bromallylate, bromomethylate, bromethylate or bromobenzylate, and the latter with its bromomethylate. Other esters specified are the piperidino-ethanol, diethylaminobutanol, morpholino-ethanol, ethylacetoxyethylamino - ethanol, ethyloxypropylamino-ethanol, methylpropylamino-ethanol and m-dimethylaminocyclohexanol esters of phenylcyclohexylacetic acid, the diethylamino-ethanol esters of phenylcyclohexylpropionic acid and phenylcyclohexylbutyric acid, the dicyclohexylacetic acid tropine ester and the α:α-dicyclohexyl-α-oxyacetic acid diethylamino-ethanol ester. Specification 448,181 is referred to. The Specification as open to inspection under Sect. 91 also describes the production of both alkamine esters and amides of alicyclic or arylalicyclic fatty acids by treating with a reducing agent an alkamine ester or amide of a fatty acid containing one or more unsaturated nuclei, followed if desired by the conversion of the product into its quaternary salt. Reference is made to the treatment of. the. alkamine esters and amides of phenyl-fatty acids and naphthalene-fatty acids. An example is present of the conversion of diphenylacetic acid - 2 - diethylaminoethylamide into the corresponding amides first of phenylcyclohexylacetic acid and then of dicyclohexylacetic acid by catalytic hydrogenation in the presence of activated platinum. The following products are also referred to : alkamine esters of dicyclopentylacetic acid, α-cyclohexylhydracrylic acid tropine ester, α-phenyl-α- cyclohexyl-α-oxyacetic acid diethylaminoethanol ester, α-cyclohexylhydracrylic acid scopine ester, α-cyclohexyl-α-propylacetic acid diethylaminoethanol ester, cyclohexylacetic acid diethylaminoethanol ester, phenylcyclohexylacetic acid ergonine methyl ester, phenyl-dimethylaminocyclohexylacetic acid diethylaminoethanol ester and cyclohexyl-diethylaminoethylacetic acid diethylaminoethanol ester. α-Cyclohexylhydracrylic acid and α- cyclohexyl a-propylacetic acid are stated to be obtained by reduction of tropic acid and α- phenyl-α-propylacetic acid respectively with hydrogen in presence of platinum, and α:α- dicyclohexyl-α-oxyacetic acid by catalytic reduction of benzilic acid. Specification 438,659 is referred to in connection with the preparation of the parent materials. This subject-matter does not appear in the Specification as accepted.