Hydrochloric Acid → N-[(4-Phenylpiperidin-4-yl)methyl]methanesulfonamide Hydrochloride
Reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][CH2:13][C:12]([CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)=O)(C)(C)C>CO>[ClH:1].[C:15]1([C:12]2([CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:11][CH2:10][NH:9][CH2:14][CH2:13]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
4
Procedure
Methanolic hydrogen chloride (4M, 40 mL) was added to a stirred, cooled (0° C.) suspension of N-[(1-t-butoxycarbonyl-4-phenylpiperidin-4-yl)methyl]methanesulfonamide (5.65 g, 15.4 mmol) in methanol (20 mL) and the mixture was stirred at room temperature for 20 h. The solvent was evaporated under reduced pressure to give the title compound as a tan solid (4.66 g, 100%), δH (250 MHz, d6 -DMSO) 9.05 (1H, br s), 8.86 (1H, br s), 7.41-7.26 (5H, m), 6.95 (1H, t, J 6.9 Hz), 3.18 (2H, m), 3.05 (2H, d, J 6.9 Hz), 2.70 (2H, m), 2.64 (3H, s), 2.26 (2H, m), and 2.02 (2H, m).