3-Methoxyacetophenone → N-[3-methyl-3-(3-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine

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In a similar fashion, 3-chloroacetophenone was used to prepare 3-methyl-3-(3-chlorophenyl)cinnamonitrile. The nitrile was catalytically reduced (palladium hydroxide, acetic acid, 60 p.s.i. hydrogen 2 hr) to generate 3-methyl-3-(3-chlorophenyl)propylamine. An equal molar amount of the amine, 3′-methoxyacetophenone and 1.25 molar equivalents titanium(IV) isopropoxide were mixed 4 hr at rt and the intermediate imine treated with an ethanolic sodium cyanoborohydride (5 ml of 1 M, 5 mmol). Work-up and chromatography afforded N-[3-methyl-3-(3-chlorophenyl)propyl]-1-(3-methoxyphenyl)ethylamine, 4Z/5A, as an oil; m/z (rel. int.) 283 (M+, 17), 268 (71), 164 (13), 135 (100), 121 (21), 105 (27), 91 (26), 77 (14).

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