Clopidogrel bisulfate → Clopidogrel

HRID 1401048Notes

Reaction equation

HRID 1401048 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 99.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
27.5 °C

Procedure

Suspension of Clopidogrel hydrogen sulfate (660 gms) was stirred in dichloromethane (3900 ml) & subsequently basified with NaHCO3 solution (10%, 6500 ml). The reaction mixture was stirred at 25 to 30° C. for about 10 minutes. The layers were separated and the aqueous layer was extracted with dichloromethane (650 ml.) and washed with water (1300 ml.). It was then dried over Na2SO4 and the solvent was distilled off on a water bath at 50 to 55° C. to obtain Clopidogrel free base (505 gms).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with dichloromethane (650 ml.)
  3. washwashed with water (1300 ml.)
  4. dry with materialIt was then dried over Na2SO4
  5. distillationthe solvent was distilled off on a water bath at 50 to 55° C.

Sources & evidence

ORD record
ord-4e85a3eb3b84473f9e9373452d59eaa2
Source dataset
uspto-grants-2014_12
Patent number
US08907090B2

Reaction notes

Loading…