Sodium Hydroxide → 2-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acid

HRID 713428Notes

Reaction equation

HRID 713428 reaction equation
C([O:3][C:4](=[O:22])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:21])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+]>CCO.O>[CH3:20][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([CH:9]2[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:22])=[O:3])[CH2:7][CH2:8]2)=[O:21])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71227128[4-(4-Methoxybenzoyl)piperidin-1-yl]acetic acid ethyl ester

Product 1

HCID 712267662-(4-(4-Methoxybenzoyl)piperidin-1-YL)acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of [4-(4-methoxy-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester (11.7 g, 38 mmol, 1 eq.) in 154 mL of EtOH was added a solution of NaOH (3.07 g, 77 mmol, 2 eq.) in 154 mL of H2O. The resulting mixture was stirred at room temperature overnight. After 18 h, the reaction mixture was concentrated and treated with 1 N HCl to pH 5. The resulting mixture was freeze dried using lyophilizer to remove H2O. The resulting yellow solids were washed with dichloromethane/methanol and filtered off NaCl. The filtrate was concentrated to give the title compound as a white solid (11 g, 38 mmol). Exact mass calculated for C15H20N1O4 278.1. MS (ESI) m/z 278.8 (M+H)+.

Workup

  1. waitAfter 18 h
  2. concentrationthe reaction mixture was concentrated
  3. additiontreated with 1 N HCl to pH 5
  4. customdried
  5. customto remove H2O
  6. washThe resulting yellow solids were washed with dichloromethane/methanol
  7. filtrationfiltered off NaCl
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8fa3ba00a01c4c7490150f24d63b17a9
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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