Studies on Aromatic Basic Ethers with Antispasmodic Activity. II. Synthesis and Anticholinergic Activities of Alkyl or Aryl 3-(N, N-Disubstituted Amino)-1-phenylpropyl Ether Derivatives

Abstract

Alkyl or aryl 1-phenyl-3-piperidinopropyl ethers (2) and alkyl or aryl 3-(2-methylpiperidino)-1-phenylpropyl ethers (3) were systematically synthesized. These newly synthesized 68 compounds were subjected to anticholinergic and mydriatic examination. 2-Chlorophenyl 3-(2-methylpiperidino)-1-phenylpropyl ether methoiodide (64a) and 3-(2-methylpiperidino)-1-phenylpropyl 2-tolyl ether methobromide (61) showed one-half the anticholinergic activity of atropine sulfate and also 30-50 times the antibarium activity of papaverine hydrochloride.