HCID 69217729, compound → HCID 69217766, compound

Participants

Reaction Steps

N-[4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenyl](phenylmethoxy)carboxamide (4.88 g, 8.68 mmol) was dissolved in ethanol (150 mL) and hydrogenated over palladium on carbon (10%, 980 mg) for 2.5 h. The reaction mixture was filtered through celite filter aid, washing with ethanol and the filtrate was concentrated in vacuo. Flash column chromatography (silica gel 60) eluting with cyclohexane:ethyl acetate (1:1 then 1:4) provided 4-methyl-3-(1-{[4-(2,4,5-trifluorophenoxy)phenyl]methyl}(4-piperidyl))phenylamine (3.71 g, 100%). LCMS (method B): 2.14 min, 427.0 (M+H)+; 1H NMR (400 MHz, CD3OD) δ 7.63 (d, 2H, J=7.2 Hz), 7.41-7.33 (m, 2H), 7.27-7.23 (m, 2H), 7.15 (d, 1H, J=8.0 Hz), 7.09 (d, 2H, J=8.0 Hz), 4.36 (s, 2H), 3.61 (d, 2H, J=12.0 Hz), 3.22 (t, 3H, J=12.0 Hz), 2.42 (s, 3H), 2.15-2.02 (m, 4H).

Provenance & Evidence