Lithium Hydroxide → [1-(4-Acetyl-phenyl)-piperidin-4-YL]-acetic acid

Reaction equation

C([O:3][C:4](=[O:21])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)C.[OH-].[Li+]>C1COCC1.O>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([N:9]2[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:21])=[O:3])[CH2:7][CH2:8]2)=[CH:13][CH:14]=1)(=[O:20])[CH3:19]

Participants

Procedure

To a solution of [1-(4-acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester (20.5 mol) in THF (10 mL) and water (20 mL) is added lithium hydroxide (41 mmol). The resulting mixture is stirred at rt overnight. The organic solvent is evaporated, and the residue is acidified to pH=4-5. The solid is collected by filtration, washed with water and dried at 60° C. in vacuo to give the title compound. 1H NMR (300 MHz, CDCl3) δ 7.86 (2H, d), 6.86 (2H, d), 3.90 (2H, br, d), 2.90 (2H, dt), 2.52 (3H, s), 2.34 (2H, d), 2.04 (1H, m), 1.88 (2H, br, d), 1.39 (2H, ddd); LC-MS (M+1) 262.