Acetic Anhydride → 4-(1-Acetylpiperidin-4-yl)benzoic acid

Participants

Reaction Steps

To a solution of 4-piperidin-4-yl)-benzoic acid (102 mg, 0.5 mmol, reference example 109) dissolved in pyridine (2 mL) was added acetic anhydride (255 mg, 2.5 mmol) and the reaction stirred overnight at room temperature. The reaction was concentrated in vacuo and residual pyridine partially removed by azeotroping with dichloromethane/methanol 1:1. The crude product was then washed with dichlormethane and the solvent decanted to yield a white solid residue (61 mg, 49%) 4-(1-acetyl-piperidin-4-yl)-benzoic acid. 1H NMR (CD3OD): δ 7.89 (d, 2H); 7.27 (d, 2H); 4.65 (d, 1H); 4.03 (d, 1H); 3.21 (dt, 2H); 2.68-2.88 (m, 2H); 1.93 (s, 3H); 1.85-2.04 (m, 2H); 1.50-1.75 (m, 3H). MS m/z 248 (M+H)+.

Provenance & Evidence