SYNTHESIS OF ANTICHOLINERGIC COMPOUNDS α-CY-CLOPENTYLPHENYLMETHOXY-ALKYLAMINES

A series of α-cyclopentylphenylmethoxyalkylamines were synthesized. Cyclopentyl phenyl ketone was obtained by Grignard reaction of bromocy clopentane and benzonitrile. When cyclopentyl phenyl ketone was reduced by lithium aluminum hydride it gave the pure alcohol correspondingly, and the yield was higher than that of any previous methods. Dehydration of α-cyclopentylphenylmethanol would take place in the presence of acid and a similar intra-molecular elimination of α-cyclopentyl-α-chloro-toluene would occur in the presence of base, both forming benzalcyclopentane. Compounds Ⅳ-1～Ⅳ-4 were obtained by 1 mole of α-cyclopentylphenylmethanol reacting with 1 mole of chloroaminoalkanes in the presence of 1.1 mole of sodium hydride, yields 40～80%; 1 mole of α-cyclopentyl-α-chloro-toluene reacted with 2 mole of alkamines to give compounds Ⅳ-5～Ⅳ-9 in yields of 17～37%. The hydrochlorides or oxalates and methyl iodides of the compounds exhibited anticholinergic activities in mice.