Pentanal → HCID 44181560, compound

Participants

Reaction Steps

A mixture of compound benzyl 4-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (400 mg, 1.1 mmol), Pd/C (10% wt, 40 mg), pentanal (114 mg, 1.6 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 the crude product. The crude product was purified by pre-HPLC to give the compound 2-(1-pentylpiperidin-4-yl)benzo[d]oxazol-7-carboxamide (44 mg, yield 14%). 1H-NMR (400 MHz, CDCl3) δ (ppm): 0.91-0.97 (m, 3H), 1.25-1.37 (m, 4H), 1.50-1.57 (m, 2H), 2.03-2.21 (m, 6H), 2.36-2.40 (m, 2H), 3.00-3.06 (m, 3H), 6.11 (s, 1H); 6.99 (s, 1H), 7.85-7.87 (t, 1H), 7.87-8.06 (m, 1H), 8.08 (dd, 1H); LC-MS (ESI) m/z: 316 (M+1)+.

Provenance & Evidence