Trifluoroacetic acid → N-{3-[1-(3-amino propyl)4-piperidinyl]phenyl}acetamide

Participants

Reaction Steps

Trifluoroacetic acid (1.0 mL) was added to a solution of tert-butyl 3-{4-[3-(acetylamino)phenyl]-1-piperidinyl}propylcarbamate (340 mg) in dry dichloromethane (10 mL) and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was basified to pH 12 by addition of a 10% aqueous solution of KOH and then the dichloromethane was removed in vacuo. The aqueous layer was frozen and lyophilized to give a solid, which was extracted with methanol. Removal of the solvent gave the desired product (120 mg) as an oil: 1H NMR (400 MHz, CDCl3) δ 7.48 (m, 1H), 7.38 (d, 1H, J=7.7 Hz), 7.24 (t, 1H, J=7.7 Hz), 6.99 (d, 1H, J=7.7 Hz), 3.11 (d, 2H, J=11.6 Hz), 2.84 (t, 2H, J=6.6 Hz), 2.59–2.52 (m, 1H), 2.50 (t, 2H, J=6.6 Hz), 2.18–2.09 (m, 2H), 2.13 (s, 3H), 1.90–1.72 (m, 6H).

Provenance & Evidence