Hydrochloric Acid → 1-(3-Methoxy-benzyl)-piperidine-2-carboxylic acid

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[C:13]([O:15]CC)=[O:14].[OH-].[Na+].Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:18]=[CH:19][CH:20]=1)[CH2:6][N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[C:13]([OH:15])=[O:14]

Participants

Procedure

A solution of ethyl 1-(3-methoxybenzyl)-2-piperidinecarboxylate (3.0 g) and 1N NaOH (21.6 ml) in ethanol (31.6 ml) was stirred at 70° C. overnight. The reaction mixture was cooled to room temperature, acidified with 1N hydrochloric acid, and evaporated in vacuo. The residue was extracted with methylene chloride and the extract was evaporated in vacuo to afford 1-(3-methoxybenzyl)-2-piperidinecarboxylic acid (2.64 g) as an amorphous powder. (+) APCI-MS (m/z): 250 (M+ +1) mp: 186.0-187.3° C. IR (Film): 1600, 1265 cm-1NMR (CDCl3, δ): 1.3-1.85 (6H, m), 2.2-2.3 (1H, m), 2.86-2.93 (1H, m), 3.09 (1H, dd, J=7.6, 4.3 Hz), 3.52 (1H, d, J=13.4 Hz), 3.74 (3H, s), 3.87 (1H, d, J=13.4 Hz), 6.81-6.93 (3H, m), 7.24 (1H, d, J=8.0 Hz)