1-Chloro-4-(trifluoromethyl)benzene → Fluoxetine

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An improved process for the preparation in a superior yield of the hydrochloride salt of N-methyl-3-(p-trifluoro-methylphenoxy)-3-phenylpropylamine of formula (I), ##STR9## said process comprising catalytically hydrogenating 2-benzoyl-1-(N-benzyl-N-methyl)ethylamine base of formula (II), ##STR10## with the aid of a catalyst selected from the group consisting of Pt/C, Pd/C and Pd-Pt/C in ethyl acetate at a hydrogen pressure of 1 to 20 bar and at a temperature of approximately 20° to 100° C. whereby 1-phenyl-3-(N-methylamino)-propan-1-ol of formula (III) is formed, ##STR11## and selectively etherifying the compound of formula (III) with 1-chloro-4-trifluoromethylbenzene of formula (IV), ##STR12## in a solvent selected from the group consisting of N-methylpyrrolidone and dimethylsulfoxide in the presence of potassium t-butoxide, whereby N-methyl-3-(p-trifluoromethylphenoxy)-3-phenylpropylamine is formed in a yield greater than 85 percent of the theoretical value and is converted to the hydrochloride salt.

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