GB818339A - Tertiary amines - Google Patents

Abstract

The invention comprises compounds of the formula <FORM:0818339/IV (b)/1> and acid addition and quaternary salts thereof, wherein R1 and R2 are alkyl, hydroxyalkyl, cycloalkyl, aryl or aralkyl groups or together with the nitrogen atom form a ring which may contain a further hetero atom, e.g. piperidino, pyrrolidino or morpholino, R3 is an alkyl group of 1-4 carbon atoms, R4 is hydrogen or an alkoxy group of 1-4 carbon atoms, Z is a straight or branched alkylene chain of 1-4 carbon atoms and R5 is hydrogen or an alkyl or alkoxy group of 1-3 carbon atoms. The compounds are prepared by treating an a -aminoacetonitrile of the formula <FORM:0818339/IV (b)/2> with an organo-magnesium halide of the formula Hal-Mg-Z-C6H4-R5, in a solvent such as diethyl ether, dibutyl ether, benzene, tetrahydrofuran, dioxan or a mixture of such solvents, preferably at an elevated temperature, and acidifying the reaction mixture to isolate the product, which may be quaternized if desired or separated as the acid addition salt. The products are used pharmaceutically as spasmolytic and local anaesthetic agents, suitably in the form of acid addition salts such as the hydrohalides, sulphates, phosphates, citrates and tartrates, or as quaternary salts derived for example from methyl or benzyl halides. Preferred compounds include 1 - (2 - n - propoxyphenyl) - 1 - diethylamino - 3 - methyl - 3 - phenyl - propane, 1 - (2-ethoxy - 3 - methoxy - phenyl) - 1 - piperidino-3 - methyl - 3 - phenyl - propane, 1 - (2 - ethoxyphenyl) - 1 - diethylamino - 3 - methyl - 3-phenyl - propane, 1 - (2 - n - propoxy - phenyl)-1 - dimethylamino - 3 - methyl - 3 - phenyl - propane and 1 - (2 - n - propoxy - phenyl) - 1 - dimethylamino - 4 - phenyl - butane. Many other products are specified and detailed examples are given.