Collect. Czech. Chem. Commun. 1981, 46, 1280-1287

1-[3-(2-Alkoxyphenoxy)-3-phenylpropyl]piperazines and some related compounds

Vladimír Valenta, Marie Bartošová and Miroslav Protiva

Research Institute for Pharmacy and Biochemistry, 130 60 Prague 3


Amino alcohols VIIIa-c, prepared by reduction of the Mannich bases VIa-c, were transformed by treatment with thionyl chloride to the chloro derivatives IXa-c which were subjected to substitution reactions with the sodium salts of guaiacol, 2-ethoxyphenol and 2-benzyloxyphenol giving the title compounds IIIb,c, IVb,c and Va-c. N,N-Dimethyl-3-(2-benzyloxyphenoxy)-3-phenylpropylamine (Va) was partially demethylated by treatment with ethyl chloroformate and by the following alkaline hydrolysis to the secondary amine XI. Amines III-V and XI in high doses exhibit central excitation but do not show antireserpine activity; they have several structurally less specific effects (hypotensive, local anaesthetic, spasmolytic).