Sodium Hydroxide → [4-(2-Trifluoromethoxy-benzoyl)-piperidin-1-yl]-acetic acid

HRID 713430Notes

Reaction equation

HRID 713430 reaction equation
C([O:3][C:4](=[O:25])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12](=[O:24])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][C:20]([F:23])([F:22])[F:21])[CH2:8][CH2:7]1)C.[OH-].[Na+]>CCO.O>[F:22][C:20]([F:21])([F:23])[O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]([CH:9]1[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:25])=[O:3])[CH2:7][CH2:8]1)=[O:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 71226626[4-(2-Trifluoromethoxy-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester

Product 1

HCID 71236044[4-(2-Trifluoromethoxy-benzoyl)-piperidin-1-yl]-acetic acidYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of [4-(2-trifluoromethoxy-benzoyl)-piperidin-1-yl]-acetic acid ethyl ester (0.36 g, 1 mmol, 1 eq.) in 5 mL of EtOH was added a solution of NaOH (0.08 g, 2 mmol, 2 eq.) in 5 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 a 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 (0.33 g, 99%). Exact mass calculated for C15H19F3N1O4332.1. MS (ESI) m/z 332.4 (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-ccf221dc0a464ee197798c36e0843e51
Source dataset
uspto-grants-2015_11
Patent number
US09181266B2

Reaction notes

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