Propanal → 2-(2-Fluoro-4-(1-propylpiperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide

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Reaction Steps

A solution of 2-(2-fluoro-4-(piperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (70 mg, 0.2 mmol), 10% Pd/C (30 mg) and propanal (5 mL, 2 mmol) in methanol (10 mL) was purged with hydrogen at room temperature for 2 days. The resulting solution was filtered and the filtrate was concentrated, the residue was purified by prep-HPLC to obtain 2-(2-fluoro-4-(1-propylpiperidin-4-yl)phenyl)benzo[d]oxazole-7-carboxamide (7.4 mg, yield 10%). 1H-NMR (400 MHz, CD3OD) δ (ppm): 1.03-1.08 (m, 3H), 1.80-1.86 (m, 2H), 2.01-2.04 (m, 2H), 2.20-2.24 (m, 2H), 3.07-3.18 (m, 5H), 3.72-3.75 (m, 2H), 7.32-7.37 (m, 2H), 7.52-7.56 (t, J=7.6 Hz, 1H), 7.94-7.97 (t, J=7.6 Hz, 2H), 8.30-8.34 (t, J=7.6 Hz, 1H); LC-MS (ESI) m/z: 382 (M+1)+.

Provenance & Evidence