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

HRID 2262706Notes

Reaction equation

HRID 2262706 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

5

Reactant 2

HCID 3939Lithium HydroxideHCID 57442326[1-(4-Acetyl-phenyl)-piperidin-4-yl]-acetic acid ethyl ester

Product 1

HCID 49759600[1-(4-Acetyl-phenyl)-piperidin-4-YL]-acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customThe organic solvent is evaporated
  2. filtrationThe solid is collected by filtration
  3. washwashed with water
  4. customdried at 60° C. in vacuo

Sources & evidence

ORD record
ord-db3c2aa3340144bf8437a64d460ac7c6
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

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