Hydrochloric Acid → 1-Benzoylpiperidine-4-carboxylic acid

HRID 617192

Reaction equation

HRID 617192 reaction equation
[NH:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>O>[C:16]([N:1]1[CH2:9][CH2:8][CH:4]([C:5]([OH:7])=[O:6])[CH2:3][CH2:2]1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 37734-Piperidinecarboxylic acidHCID 7412Benzoyl chlorideHCID 11430Potassium Carbonate

Product 1

HCID 789351-Benzoylpiperidine-4-carboxylic acidYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To an ice cold solution of isonipecotic acid (90 g, 0.697 mol) and potassium carbonate (81 g, 1.31 mol) in water (1.3 liter) was added dropwise benzoyl chloride (81 ml, 0.697 mol) over a period of about an hour at about 5° C. The mixture was stirred at room temperature overnight. The reaction mixture was acidified with 6N hydrochloric acid and extracted with dichloromethane. The organic layer was washed with water and then dried over magnesium sulfate and the solvent was evaporated in vacuo. Crystallization from isopropyl alcohol-diethyl ether to give the titled compound (154.4 g).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent was evaporated in vacuo
  5. customCrystallization from isopropyl alcohol-diethyl ether

Sources & evidence

ORD record
ord-090031d131f24188b7adc55f41b6ba9b
Source dataset
uspto-grants-1999_09
Patent number
US05948786

Linked notes

Loading…