GB558653A - Manufacture of basic ethers - Google Patents

Abstract

558,653. Basic ethers. SOC. OF CHEMICAL INDUSTRY IN BASLE. April 8, 1942, No. 4599. Convention date, April 10, 1941. [Class 2 (iii)] Basic ethers are made by causing a disubstituted acetic acid ester, amide or nitrile, which contains a hydroxyl group in the α- position, to react with a reactive ester of an amino-alcohol, or by causing a disubstituted acetic acid ester, amide, or nitrile which contains a halogen atom in the α-position to react with an amino-alcohol. Disubstituted acetic acid derivatives which contain aromatic, cycloaliphatic or alipbatic residues as substituents, e.g. α, α<SP>1</SP>-diphenyl-α-hydroxyacetic acid esters, α-phenyl-α-alkyl-α-hydroxyacetic acid esters, α-phenyl-α-cyclohexyl-α-hydroxyacetic esters, α, α-dicyclohexyl-α-hydroxyacetic acid esters, or the corresponding α-halogen derivatives or their nitriles or amides may be used. Amino-alcohols include dialkylaminoalkanols, piperidino-alkanols, dialkyl-aminocyclohexanols, tropines and esters thereof with hydrohalic acids, arylsulphonic acids and the like. Solvents may be used and condensing agents such as alkalis, alkali amides or alkali carbonates. Quaternary ammonium compounds of the basic ethers may be prepared by additive combination with alkyl halides, alkylene halides, arylsulphonic acid esters, dialkyl sulphates, or aryl-alkyl halides. From the nitriles the corresponding acids, esters or amides may be obtained, or the nitriles may be converted to ketimides by the Grignard method and into ketones by saponifying the latter. The products have a powerful spasmolytic action. Examples give the preparation of α, α-diphenyl- α-diethylaminoethoxy-acetic acid ethyl, methyl. and n-propyl esters, α, α-diphenyl-α-piperidinoethoxyacetic acid ethyl, methyl, and n-propyl ester, α, α-diphenyl α-tropinoxyacetic acid ester, α, α - diphenyl-x-diethylamino - propyloxyacetic acid ethyl ester, α, α diphenyl-α-diethylaminoethoxyacetonitrile, diphenyl-diethyl-aminoethoxymethyl-ethyl ketone and α, α-diphenyl-α- diethyl-aminoethoxyacetamide. α, α-Diphenyl-α-bromacetonitrile is prepared by brominating diphenylacetonitrile.