摘要 |
New compounds of formula <FORM:1046311/C2/1> where Ar is phenyl, halophenyl, lower (i.e. 1-5 C) alkylphenyl or lower alkoxyphenyl, R is hydrogen, lower alkyl, lower alkylcarbonyl, benzoyl, hydroxymethyl, halomethyl, lower alkoxymethyl, cyanomethyl or cyano- CH(R2)CH(R2)-, R2 being hydrogen or methyl, R1 is hydrogen or methyl, and n is 1 or 2, and non-toxic acid addition salts thereof, are prepared by methods comprising (1) reaction of an Ar-alkenyl-chloro or -bromo compound with a 4-substituted-piperidine, (2) introduction of a hydroxymethyl group R with formaldehyde, from which halomethyl compounds are obtained and thence alkoxymethyl or cyanomethyl compounds, (3) introduction of alkyl groups R, (4) introduction of alkylcarbonyl or benzoyl groups R, (5) introduction of cyano- CH(R2)CH(R2)- groups R using a ,b -unsaturated nitriles. Starting materials prepared are: 1-(4-fluorophenyl) - 4 - chloro - 1 - butene, 2 - phenyl - 5 - bromo - 2 - pentene, 2 - (4 - fluorophenyl) - 5 - bromo - 2 - pentene, 2 - (4 - methoxyphenyl) - 5 - chloro - 2 - pentene, 2 - (4 - chlorophenyl) - 5 - chloro - 2 - pentene and 2 - (4 - methylphenyl) - 5-chloro-2-pentene, all obtained from corresponding phenyl - cyclopropyl - carbinols with halogenating agents; dl - cyclopropyl - 4- (methoxy-, chloro-, methyl-)phenyl - methyl-carbinols are prepared from ketones and Grignard reagents. |