Triethylamine → N-(4-Chloro-phenyl)-4-{3-[4-(3,3-dimethyl-butyl)-piperazin-1-yl]-propoxy}-3-fluoro-N-methyl-benzamide

Participants

Reaction Steps

N-(4-Chloro-phenyl)-3-fluoro-N-methyl-4-(3-piperazin-1-yl-propoxy)-benzamide dihydrochloride from Example E71.2 (184 mg, 0.4 mmol) was dissolved in methanol (4.95 ml) and triethylamine (0.167 ml, 1.2 mmol). Acetic acid (0.05 ml) then 3,3-dimethylbutyraldehyde (46 mg, 0.44 mmol) were added and the mixture was stirred for 1 h at room temperature. Sodium cyanoborohydride (31 mg, 0.5 mmol) was added and the mixture was stirred for 20 h at room temperature then concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 10% methanol:90% dichloromethane) to give a white foam identified as the title compound (77 mg, 37%).

Provenance & Evidence