Potassium Hydroxide → 4-Piperidinecarboxylic acid

HRID 1434552Notes

Reaction equation

HRID 1434552 reaction equation
FC(F)(F)C1C=CC([N:9]2[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=[O:16])[CH2:11][CH2:10]2)=NC=1.[OH-].[K+]>CO.O>[NH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 4737360HCID 4737360, compound

Product 1

HCID 37734-Piperidinecarboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The crude ethyl 1-[5-(trifluoromethyl)pyridin-2-yl]piperidine-4-carboxylate was dissolved in 15 ml of methanol and 2.5 ml of water. 535 mg (9.54 mmol) of potassium hydroxide were added and the mixture was reacted at 40° C. for 30 min. The mixture was evaporated, the residue was dissolved in water, pH 3 was adjusted with 2N hydrochloric acid and the solid formed was filtered off and dried in vacuo to yield 471 mg (54% yield) of 1-[5-trifluoromethyl)pyridin-2-yl]piperidine-4-carboxylic acid.

Workup

  1. customthe mixture was reacted at 40° C. for 30 min
  2. customThe mixture was evaporated
  3. dissolutionthe residue was dissolved in water
  4. customthe solid formed
  5. filtrationwas filtered off
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a569c53e454f4008902733d2445451b0
Source dataset
uspto-grants-2009_11
Patent number
US07615557B2

Reaction notes

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