Lithium Hydroxide → 1-Phenylpiperidine-4-carboxylic acid

HRID 1178059Notes

Reaction equation

HRID 1178059 reaction equation
[Li+].[OH-].C[O:4][C:5]([CH:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:9][CH2:8]1)=[O:6]>C1COCC1.CO.O>[C:13]1([N:10]2[CH2:11][CH2:12][CH:7]([C:5]([OH:6])=[O:4])[CH2:8][CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59559569Methyl 1-phenylpiperidine-4-carboxylate

Product 1

HCID 30239901-Phenylpiperidine-4-carboxylic acidYield 67.3%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

LiOH (43 mg, 1.03 mmol) was added at room temperature to a stirred solution of 1-phenyl-piperidine-4-carboxylic acid methyl ester (150 mg, 0.68 mmol) in THF:MeOH:H2O (3:1:1, 3.2 mL). The resulting mixture was stirred at room temperature overnight. The MeOH and THF were evaporated and the residue was diluted with water (2 mL), acidified with citric acid solution and extracted with EtOAc. The organic layer was washed with saturated brine, dried over Na2SO4 and concentrated under reduced pressure to afford 94 mg (67.14% yield) of 1-phenyl-piperidine-4-carboxylic acid. LCMS purity: 95.98%.

Workup

  1. customThe MeOH and THF were evaporated
  2. additionthe residue was diluted with water (2 mL)
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-76b049cadfc14dec8fa84d59df357cba
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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