Lithium Hydroxide → 1-Phenylpiperidine-4-carboxylic acid

HRID 1177973Notes

Reaction equation

HRID 1177973 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 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), and 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 the product extracted with EtOAc. The organic layer was washed with saturated brine solution, dried over Na2SO4 and concentrated in vacuo to afford 94 mg (67.1% yield) of 1-Phenyl-piperidine-4-carboxylic acid. LCMS purity: 95.9%.

Workup

  1. customThe MeOH and THF were evaporated
  2. additionthe residue was diluted with water (2 mL)
  3. extractionthe product extracted with EtOAc
  4. washThe organic layer was washed with saturated brine solution
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1646ac55394c4c3e8f6b5aca11154fcd
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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