Propanal → HCID 44181675, compound

Participants

Reaction Steps

A mixture of benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (200 mg, 0.53 mmol), propionaldehyde (40 mg, 0.7 mmol) and 10% Pd/C (20 mg) in methanol (20 mL) was stirred at room temperature over 1 atm hydrogen for 4 hr. The mixture was filtered, and evaporated under reduced pressure. The residue was purified by prep-HPLC to give 2-(1-propylpiperidin-4-yl)benzo[d]oxazole-7-carboxamide (71 mg, yield 46%). 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 0.84-0.88 (t, J=7.2 Hz, 1H), 1.43-1.48 (m, 2H), 1.83-1.89 (m, 2H), 2.04-2.12 (m, 2H), 2.24-2.28 (m, 2H), 2.88-2.91 (m, 2H), 2.89-3.02 (m, 1H), 7.39-7.73 (t, J=7.6 Hz, 1H), 7.72-7.77 (m, 3H), 7.84-7.85 (d, J=6.8 Hz, 1H); LCMS (ESI) m/z: 288 (M+1)+.

Provenance & Evidence