Collect. Czech. Chem. Commun. 1986, 51, 1487-1493

Synthesis of N-(1-phenyl-2-propyl)-2,5-diphenylpentylamine and some related compounds as potential neurotropic and cardiovascular drugs

Zdeněk Vejdělek, Jiří Němec and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Heating of 2,5-diphenylvaleric acid with 2-phenylethylamine, 1-phenyl-2-propylamine, 1-phenyl-2-butylamine (IX), 1-(4-methoxyphenyl)-2-propylamine, 1-(4-methoxyphenyl)-2-butylamine (X) and 1-(4-dimethylaminophenyl)-2-propylamine to 200-210 °C resulted in the amides IIb-VIIb which were reduced with lithium aluminium hydride in boiling dibutyl ether to give the amines IIa, IIIa, and Va - VIIa. A similar two-step sequence starting from 4-phenyl-4-(phenylthio)-butyric acid and the amine IX gave compound VIIIa. The salts of the title amines revealed some central stimulating, antireserpine, thiopental potentiating, anticonvulsant, and antiarrhythmic effects. 1-(4-Dimethylaminophenyl)-2-butylamine (XI), prepared in this connection, proved anoretic activity.