Dichloromethane → Clopidogrel

HRID 1673061Notes

Reaction equation

HRID 1673061 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:18][C:17]2[CH:19]=[CH:20][S:21][C:16]=2[CH2:15][CH2:14]1)[C:6]1[C:11]([Cl:12])=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4].Cl.C(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:18][C:17]2[CH:19]=[CH:20][S:21][C:16]=2[CH2:15][CH2:14]1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[Cl:12])=[O:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 9798860Clopidogrel hydrochloride

Product 1

HCID 60606Clopidogrel

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under the protection of nitrogen gas, clopidogrel hydrochloride (7.15 g) was introduced into methylene dichloride (100 ml) in a 250 ml flask under stirring and cooling with ice water. Then a solution of potassium carbonate (2.5 g) in de-ionized water (30 ml) was added drop by drop into the flask and it was stirred for one hour. The pH value of the upper aqueous phase was kept over 9. The lower organic phase was separated and the aqueous phase was extracted with methylene dichloride (50 ml). The organic phases were combined and dried over sodium sulfate and then concentrated to obtain a free clopidogrel base.

Workup

  1. stirringwas stirred for one hour
  2. customThe lower organic phase was separated
  3. extractionthe aqueous phase was extracted with methylene dichloride (50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-da6f826fad2546f5a6addd043d44c31c
Source dataset
uspto-grants-2011_08
Patent number
US07999106B2

Reaction notes

Loading…