GB1025041A - Process for the manufacture of diphenylalkylamines - Google Patents

Abstract

Diphenylalkamines of the formula <FORM:1025041/C2/1> and salts thereof, wherein R1 and R2 are each hydrogen, C1- 3 alkyl, C1- 3 alkoxy or halogen, R3 is hydrogen or C1- 3 alkyl and R4 is hydrogen, C1- 4 alkyl or an aralkyl group having 1-4 carbon atoms in the alkylene chain, which may be substituted in the phenyl nucleus by C1- 3 alkyl or C1- 3 alkoxy groups, or NR3R4 forms a morpholino, piperidino or pyrrolidino ring, and n is 1 or 2, are made by reacting an o -phenyl-o -hydroxy-alkylamine or an o -phenyl-o -halo-alkylamine or a styryt or cinnamyl-amine with an aryl compound C6H5R2, in the presence of a Friedel-Crafts catalyst, such as alminium-trichloride, gallium trichloride or boron tri fluoride. 1 - Phenyl - 1 - chloro - 3 - (1 - phenyl - propyl-(2) - amino) - propane is made by reacting 1 - phenyl - 1 - hydroxy - propylamine - (3) with phenylacetone, reducing with sodium boron hydride and treating the resulting 1-phenyl-1-hydroxy - 3 -(1 - phenyl - propyl - (2) - amino)-propane (hydrochloride) with thionyl chloride. 1 - Phenyl - 1 - chloropropylamine is made by the action of thionyl chloride on 1 -phenyl-1-hydroxy - propylamine. 1 - Phenyl - 1 - hydroxy-2 - (1 - phenyl - propyl - (2) - amino) - ethane is made by the reaction of styrene oxide with 1-phenyl - propylamine (2). 1 - Phenyl - 2 -cinnamylamino-propane hydrochloride is made by condensing cinnamic aldehyde with 1-phenyl-propyl-amine-(2) and reducing the resulting Schiffs base with sodium boron hydride.ALSO:Pharmaceutical preparations having action on the cardiac and circulatory system comprose compounds of the formula <FORM:1025041/A5-A6/1> wherein R1 and R2 are each hydrogen, halogen or a C1-3 alkyl or alkoxy group, R3 is hydrogen or a C1-3 alkyl group and R4 is hydrogen, a C1-4 alkyl group or an aralkyl group having up to 4 carbon atoms in the alkylene chain optionally bearing C1-3 alkyl or alkoxy substituents on the alkylene chain, or NR3R4 forms a morpholino, piperidino or pyrrolidino ring and n is 1 or 2, or physiologically tolerable salts thereof with organic or inorganic acids, in admixture or conjunction with an excipient. The preparations may take forms suitable for parenteral or oral administration e.g. tablets.