Lithium Hydroxide → 4-Piperidin-1-yl-3-(trifluoromethyl)benzoic acid

HRID 336268Notes

Reaction equation

HRID 336268 reaction equation
[OH-].[Li+].[N:3]1([C:9]2[CH:18]=[CH:17][C:12]([C:13]([O:15]C)=[O:14])=[CH:11][C:10]=2[C:19]([F:22])([F:21])[F:20])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1>C1COCC1.O>[N:3]1([C:9]2[CH:18]=[CH:17][C:12]([C:13]([OH:15])=[O:14])=[CH:11][C:10]=2[C:19]([F:20])([F:21])[F:22])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67528357Methyl 4-piperidin-1-yl-3-(trifluoromethyl)benzoate

Product 1

HCID 596065494-Piperidin-1-yl-3-(trifluoromethyl)benzoic acidYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium hydroxide (2.83 g, 67.5 mmol, 2 eq.) was added to a solution of methyl 4-piperidin-1-yl-3-(trifluoromethyl)benzoate (9.7 g, 33.7 mmol, 1 eq.) in THF (50 mL) and water (5 mL) and the reaction mixture was stirred at room temperature for 12 hours. The solvent was removed in vacuo and the residue taken up in water. The aqueous layer was washed with DCM, acidified to pH 2 with conc. HCl and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to afford the title compound (3.0 g, 95%) as a white solid.

Workup

  1. customThe solvent was removed in vacuo
  2. washThe aqueous layer was washed with DCM
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6739f98a35a94b6891dd41f7d8c3b4f5
Source dataset
uspto-grants-2014_11
Patent number
US08889668B2

Reaction notes

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