1-Acetylnaphthalene → N-1-(1-naphthyl)ethyl-1-(3-methoxyphenyl)ethylamine

Participants

Reaction Steps

In a similar fashion equal molar amounts of 1-(3-methoxyphenyl)ethylamine, 1′-acetonaphthone and 1.25 equivalents of titanium(IV) isopropoxide were mixed and the resulting intermediate imine was reduced with ethanolic sodium cyanoborohydride. Work-tip and chromatography yielded N-1-(1-naphthyl)ethyl-1-(3-methoxyphenyl)ethylamine, 6E, as a clear, colorless oil; m/z (rel. int.) 305 (M+, 10), 290 (30), 170 (43), 155 (100), 135 (69), 115 (9), 105 (15), 91 (14), 77 (18).

Provenance & Evidence