Methanol → HCID 68509584, compound

Participants

Reaction Steps

Acetyl chloride (0.71 mL, 0.79 g, 10.0 mmol) was added dropwise to a stirred, cooled (0° C.) solution of N-phenyl-1-t-butoxycarbonylpiperidine-4-methylamine (2.42 g, 8.3 mmol), pyridine (1.01 mL, 0.99 g, 12.5 mmol) and 4-dimethylaminopyridine (204 mg, 1.7 mmol) in dichloromethane (50 mL) and the mixture was stirred at room temperature for 1 h. Methanol (5 mL) was added and the solvent was evaporated under reduced pressure. Aqueous sodium hydrogen carbonate (saturated, 50 mL) was added and the mixture was extracted with ethyl acetate (3×50 mL). The combined organic fractions were washed with aqueous citric acid (10%, 2×50 mL), aqueous sodium hydrogen carbonate (saturated, 50 mL) and brine (50 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure to give the title compound as a colorless solid (2.73 g, 99%), δH (250 MHz, CDCl3) 7.47-7.15 (5H, m), 4.06 (2H, br m), 3.62 (2H, br m), 2.64 (2H, br m), 1.85 (3H, s), 1.66 (3H, m), 1.44 (9H, s), and 1.20 (2H, m).

Provenance & Evidence