Butanal → HCID 44181559, compound

Participants

Reaction Steps

A mixture of benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (400 mg, 1.06 mmol), Pd/C (10% wt, 40 mg), butyraldehyde (96 mg, 1.58 mmol) in anhydrous methanol (15 mL) was purged with hydrogen at room temperature for 12 hr. The mixture was filtered and the filtrate was concentrated to give crude product. The crude product was purified by prep-HPLC to give 2-(1-butylpiperidin-4-yl)benzo[d]oxazol-7-carboxamide (44 mg, yield 13%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 0.94 (t, 3H), 1.30-1.48 (m, 2H), 1.48-1.55 (m, 2H), 2.03-2.11 (m, 6H), 2.36-2.41 (m, 2H), 3.00-3.06 (m, 3H), 6.20 (s, 1H); 6.99 (s, 1H), 7.42-7.46 (t, 1H), 7.85-7.87 (m, 1H), 8.07 (dd, 1H); LC-MS (ESI) m/z: 302 (M+1)+.

Provenance & Evidence