2-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone → alpha-[[[5-[2-(4-Fluorophenyl)ethoxy]pentyl]amino]methyl]-4-hydroxy-3-(methoxy methyl)benzenemethanol

Participants

Reaction Steps

A solution of 2-bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone (1.0 g), N-[5-(2-(4-fluorophenyl)ethoxy]pentyl]benzenemethanamine (0.91 g), and DEA (0.77 g) in THF (15 ml) was left at room temperature for 18 h, filtered and evaporated. The residue was hydrogenated over 10% Pd-C (0.5 g) and 5% Pt-C (0.5 g), filtered and evaporated. The resulting oil was purified by FCC eluting with System C (80:20:1) to give the title compound as a white solid (0.58 g) m.p. 86°-87°, t.l.c. (System C 80:20:1) Rf 0.25.

Provenance & Evidence