Benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate → 2-(Piperidin-3-yl)benzo[d]oxazole-7-carboxamide

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Reaction Steps

A mixture of benzyl 3-(7-carbamoylbenzo[d]oxazol-2-yl)piperidine-1-carboxylate (100 mg, 0.26 mmol), 10% Pd/C (20 mg) in methanol (30 mL) was stirred at room temperature over 1 atm hydrogen for 2 hr. The mixture was evaporated under reduced pressure and purified by pre-HPLC to give 16 mg of 2-(piperidin-3-yl)benzo[d]oxazole-7-carboxamide as a solid. Yield 25%. 1H-NMR (400 MHz, DMSO-d6): δ 1.50-1.53 (m, 1H), 1.65-1.67 (m, 1H), 1.81-1.84 (m, 1H), 2.16-2.19 (m, 1H), 2.50-2.54 (m, 1H), 2.81-2.90 (m, 2H), 3.07-3.12 (m, 1H), 3.28-3.31 (m, 1H), 7.39-7.43 (t, J=8.0 Hz, 1H), 7.72-7.78 (m, 3H), 7.83-7.85 (m, 1H). LC-MS (ESI) m/z: 246 (M+1)+.

Provenance & Evidence