Patent ID: 6541668
Filing Date: 2003-04-01
Classification: C07C

Abstract:
A process for preparing 3-aryloxy-3-arylpropylamines of the formula whereinAr is phenyl or 2-thienyl, Ar1 is 1-naphthyl, 2-methoxyphenyl, 2-thiomethoxyphenyl, or 2-methylphenyl; G is hydrogen or methyl, and the pharmaceutically-acceptable addition salts thereof comprising the steps of:(a) reacting an alkoxide of a 3-hydroxy-3-arylpropylamine of the formula â€ƒwherein Ar and G are as defined above with a haloaromatic of the formula Ar1â€”X â€ƒwherein Arl-X is 2-fluorotoluene, 2-chlorotoluene, 1-fluoronaphthalene, 1-chloronaphthalene, 2-fluoroanisole, 2-chloroanisole, 2-fluorothioanisole, or 2-chlorothioanisole, in 1,3-dimethyl-2-imidazolidinone or N-methylpyrrolidinone at a temperature of from 0Â° C. to 140Â° C. to give the 3-aryloxy-3-arylpropylamine; (b) N-demethylat of the 3-aryloxy-3-arylpropylamine wherein G is methyl to give the 3-aryloxy-3-arylpropylamine wherein G is hydrogen; (c) optional resolution of the 3-aryloxy-3-arylpropylamine to give a specific isomer of the 3-aryloxy-3-arylpropylamine; and (d) optional formation of an acid addition salt using a pharmaceutically-acceptable acid.