Synthesis of several 1-(aminoacyl)-4-cinnamylpiperazines as potential analgetics

Abstract

A reaction of 1-cinnamylpiperazine (III) with chloroacetyl gave the chloroacetyl derivative IV which was subjected to substitution reactions with aniline, 4-phenylpiperidin-4-ol (XIa),4-(4-fluorophenyl)piperidin-4-ol (XIb) and 4-(4-chloro-3-trifluoromethyl)piperidin-4-ol and afforded the title compounds V and VII-IX. Acylation reactions of compounds V and VII with propionyl chloride gave the propionanilide derivative VI and the 4-phenyl-4-propanoyloxypiperidine derivative X. With the exception of compound VIII, the new substances are analgetically less active than 1-butyryl-4-cinnamylpiperazine (I) and as antiinflammatory agents they are little active or inactive.