GB1112526A - Alkoxy-trifluoromethylphenalkylamines - Google Patents

Abstract

The invention comprises a secondary amine of the formula <FORM:1112526/C2/1> wherein R is b -hydroxyethyl or hydrocarbyl containing 1-8 carbon atoms and A is a 1-3 carbon atom alkylene bridge containing a total of 1-8 carbon atoms, and the phenyl nucleus may be optionally substituted by additional substituents, e.g. alkyl, aryl, alkaryl, halo, CF3, OH or NO2, preferably in the 2, 4, 5 or 6 position, and acid addition salts thereof. The secondary amine may be prepared by converting a trifluoromethyl substituted phenyl bromide of the corresponding Grignard reagent, reacting the reagent with a lower alkyl a ,o -dihalo-lower-alkyl ether to form a trifluoromethylphenalkyl halide bearing a lower alkoxy group on the carbon atom alpha to the phenyl ring and reacting said halide with a primary amine. Alternatively, the said halide may be reacted with ammonia to form the corresponding primary amine which is reacted with a hydrocarbon halide having 1-8 carbon atoms or with ethylene oxide. a ,q -Dichloropropyl methyl ether is made by passing HCl through a stirred mixture of acrolein and methanol at 0 DEG C. Pharmaceutical compositions, having antiemetic, sedative, mydriatic and nicotine antagonistic activity, comprise the above compounds in association with a pharmaceutically acceptable diluent, excipient or carrier in forms suitable for oral, subcutaneous, intravenous and intraperitoneal administration.