Potassium Hydroxide → 1-(3-Chlorophenyl)-4-piperidinecarboxylic acid

HRID 1434550Notes

Reaction equation

HRID 1434550 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH2:12][CH:11]([C:14]([O:16]CC)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[OH-].[K+]>CO.O>[Cl:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:9][CH2:10][CH:11]([C:14]([OH:16])=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 57936084HCID 57936084, compound

Product 1

HCID 579360781-(3-Chlorophenyl)-4-piperidinecarboxylic acidYield 90%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

158 mg (0.59 mmol) of ethyl 1-(3-chlorophenyl)-piperidine-4-carboxylate were dissolved in 2.30 ml of methanol and 0.3 ml of water, and 99 mg (1.77 mmol) of powdered potassium hydroxide were added. The mixture was stirred at room temperature overnight After evaporation of the solvent, water was added and the mixture was acidified to pH 2-3 with 2N hydrochloric acid. The aqueous phase was extracted with ethyl acetate three times, the combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and evaporated to give 127 mg (90% yield) of 1-(3-chlorophenyl)-piperidine-4-carboxylic acid.

Workup

  1. customAfter evaporation of the solvent, water
  2. additionwas added
  3. extractionThe aqueous phase was extracted with ethyl acetate three times
  4. washthe combined organic phases were washed with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-434a0e36a58a449aa9084bd5bbb3b9d8
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

Loading…