Clopidogrel bisulfate → Clopidogrel

HRID 1401046Notes

Reaction equation

HRID 1401046 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].OS(O)(=O)=O.C([O-])(O)=O.[Na+]>ClCCl>[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

4

Reactant 2

HCID 115366Clopidogrel bisulfateHCID 516892Sodium Bicarbonate

Product 1

HCID 60606ClopidogrelYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

Suspension of Clopidogrel hydrogen sulfate (61 gms) was stirred in dichloromethane (360 ml) and subsequently basified with NaHCO3 solution (10%, 600 ml). The mixture was stirred at 25 to 30° C. for about 10 minutes. The layers were separated and the aqueous layer was extracted with dichloromethane (60 ml.) and washed with water (120 ml.). It was then dried over Na2SO4 and the solvent was distilled off on a water bath at a temperature in the range from 50 to 55° C. to obtain Clopidogrel free base (46.0 gms)

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (60 ml.)
  3. washwashed with water (120 ml.)
  4. dry with materialIt was then dried over Na2SO4
  5. distillationthe solvent was distilled off on a water bath at a temperature in the range from 50 to 55° C.

Sources & evidence

ORD record
ord-83e1faaab286484a9e1583d9cb82f653
Source dataset
uspto-grants-2014_12
Patent number
US08907090B2

Reaction notes

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