GB624117A - Improvements in and relating to the preparation of substituted allylamines and propylamines - Google Patents

Abstract

Substituted allylamines of the general formula <FORM:0624117/IV (b)/1> or salts thereof, in which R1 and R2 are aryl, aralkyl or cycloalkyl groups which may be further substituted by alkyl or alkoxy groups; R1 and R2 may be identical provided that both are not aralkyl groups; R3 is hydrogen or alkyl; R4 is hydrogen, alkyl or aryl (substituted or unsubstituted as above); R5 and R6 are alkyl or aryl, or -NR5R6 may denote the piperidino-, pyrolidino- or morpholino-groups; are prepared from the corresponding N-disubstituted - g : g - disubstituted - g - hydroxy-propylamines or salts thereof by removing the elements of water by known methods for the conversion of tertiary alcohols to olefines. The allylamines may be converted into the corresponding propylamines by reduction under mild conditions. When R1 or R2 are aralkyl or cycloalkyl groups the product of dehydration is sometimes an isomer in which the double bond is attached to the a -carbon atom. In examples: (1) 3-n-piperidino-1 : 1-diphenylpropan-1-ol hydrochloride is refluxed with a mixture of concentrated hydrochloric acid and glacial acetic acid to give 3-N-piperidino-1 : 1-diphenylprop-1-ene hydrochloride which is reduced with hydrogen and a hydrogenation catalyst to give 3-N-piperidino-1 : 1-diphenylpropane; (2) 3-dimethylamino-1 : 1-diphenylpropan-1-ol is treated as in (1) to give 3-dimethylamino - 1 : 1 - diphenylprop - 1 - ene and 3-dimethylamino-1 : 1-diphenylpropane; (3) 3-diethylamino - 1 : 1 - diphenylpropan - 1 - ol hydrochloride is treated as in (2) to give the corresponding ethyl derivatives; (4) 3-N-pyrrolidino - 1 : 1 - diphenylpropan - 1 - ol is treated as in (1) to give 3-N-pyrrolidino-1 : 1-diphenylprop - 1 - ene and 3 - N - pyrrolidino-1 : 1-diphenylpropane; (5) the corresponding morpholino derivatives are used in the process of (4) to give analogous products; (6) 3-di-methylamino - 1 : 1 - diphenylbutan - 1 - ol hydrochloride is treated as in (1) to give 3-dimethylamino - 1 : 1 - diphenylbut - 1 - ene and 3 - dimethylamino - 1 : 1 - diphenylbutane; (7) 3 - diethylamino - 1 : 1 - di - p - tolylpropan-1-ol hydrochloride is treated as in (1) to give the corresponding derivatives; (8) 3-diethylamino - 1 - cyclohexyl - 1 - phenylpropan - 1 - ol is used as the starting material in the process of (1); and (9) p 3-diethylamino-1-benzyl-1-phenylpropan-1-ol hydrochloride is treated as in (1). Specification 624,118 is referred to.