Acetic Acid → HCID 11525806, compound

Participants

Reaction Steps

2-methyl-N-(4-methyl-3-(4-piperidyl)phenyl)propanamide (130 mg, 0.500 mmol) and 4-(4-fluorophenylthio)benzaldehyde (116 mg, 0.500 mmol) were dissolved in dichloroethane (5.00 mL) and acetic acid (30.0 mg, 0.500 mmol), and sodium triacetoxborohydride (212 mg, 1.00 mmol) was added at room temperature. Stirring was continued under nitrogen at room temperature for 10 h, then a saturated aqueous NaHCO3 solution and CH2Cl2 was added. The phases were separated, and the organic phase was washed with water, dried over Na2SO4 and concentrated in vacuo. Purification by flash column chromatography (eluent: cyclohexane:EtOAc (85:15 then 7:3)) gave N-[3-(1-{[4-(4-fluorophenylthio)phenyl]methyl}(4-piperidyl))-4-methylphenyl]-2-methylpropanamide (86.3 mg, 36.2% yield) as a white solid. 1H NMR (CDCl3) δ 7.43-7.32 (m, 3H), 7.31-7.22 (m, 5H), 7.09-6.98 (m, 4H), 3.51 (s, 2H), 3.04-2.93 (m, 2H), 2.76-2.61 (m, 1H), 2.52-2.41 (m, 1H), 2.27 (s, 3H), 2.14-2.03 (m, 2H), 1.86-1.65 (m, 4H), 1.25 (d, 6H, J=7.026 Hz); ESMS m/e: 477.2 (M+H)+.

Provenance & Evidence