Propanal → HCID 44181557, compound

Participants

Reaction Steps

A mixture of 2-(4-(piperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide (80 mg, 0.25 mmol) and propionaldehyde (72 mg, 1.25 mmol) in methanol (10 mL) was stirred at room temperature for 40 min. Then the mixture was cooled to 0° C. Sodium borohydride (45 mg, 0.75 mmol) was added. After the addition, the mixture was stirred at this temperature for 2 hr. Methanol was removed under reduced pressure. The residue was washed with ethyl acetate/methanol (10/1) and filtered. The filtrate was concentrated to give the crude product. The crude product was purified by pre-HPLC to give 2-(4-(1-propylpiperidin-3-yl)phenyl)benzo[d]oxazole-7-carboxamide as a light yellow solid (18 mg, yield 23%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 0.94 (t, 3H), 1.58-1.64 (m, 3H), 1.81-2.01 (m, 3H), 2.11-2.20 (m, 2H), 2.43 (m, 2H), 2.97 (m, 1H), 3.08 (t, 2H), 7.50-7.54 (m, 3H), 7.91-7.94 (m, 2H), 8.29 (d, 1H); LC-MS (ESI) m/z: 364 (M+1)+.

Provenance & Evidence