Propanal → 2-(1-Propylpiperidin-3-yl)benzo[d]oxazole-7-carboxamide

Participants

Reaction Steps

A mixture of 2-(piperidin-3-yl)benzo[d]oxazole-7-carboxamide (25 mg, 0.1 mmol), propionaldehyde (9 mg, 0.156 mmol) and 10% Pd/C (10 mg) in methanol (5 ml) was stirred at room temperature over 1 atm hydrogen for 3 h. Then the mixture solution was filtered and the filtrate was evaporated under reduced pressure. The residue was purified by prep-HPLC to obtain 2-(1-propylpiperidin-3-yl)benzo[d]oxazole-7-carboxamide (15 mg, yield 41%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 0.88-0.93 (t, J=7.2 Hz, 3H), 1.51-1.61 (m, 2H), 1.72-1.91 (m, 4H), 2.07-2.13 (m, 1H), 2.24-2.27 (m, 1H), 2.38-2.43 (t, J=8 Hz, 2H), 2.91-2.94 (d, J=11.2 Hz, 1H), 3.29-3.35 (m, 2H), 6.26 (s, 1H), 7.0 (s, 1H), 7.41-7.45 (t, J=7.6 Hz, 1H), 7.85-7.87 (d, J=7.6 Hz, 1H), 8.06-8.08 (d, J=8 Hz, 1H). LC-MS (ESI) m/z: 288 (M+1)+.

Provenance & Evidence