Water → Clopidogrel bisulfate

HRID 1401057Notes

Reaction equation

HRID 1401057 reaction equation
[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][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].O.[OH:23][S:24]([OH:27])(=[O:26])=[O:25]>C(O)CCCCCCCCC>[CH3:1][O:2][C:3]([C@@H:5]([N:13]1[CH2:21][C:17]2[CH:18]=[CH:19][S:20][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].[OH:26][S:24]([OH:27])(=[O:25])=[O:23]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 60606Clopidogrel

Product 1

HCID 115366Clopidogrel bisulfate

Reagents, catalysts & solvents 1

HCID 81741-DecanolSolvent

Conditions

Temperature
27.5 °C

Procedure

Clopidogrel base (10 gms) was dissolved in decan-1-ol (50 mL) with stirring at 25 to 30° C. and water (0.2 ml) was added to it. Concentrated H2SO4 was added at 10-15° C. Solid material precipitated. The mixture was stirred at room temperature, for 24 hrs. It was filtered, washed with methyl tert-butyl ether (30 ml) and dried at temperature in the range from 30 to 35° C. in a drier, to get 7 g of Clopidogrel bisulfate salt as crystals. Subsequent analysis confirmed that the crystals were clopidogrel hydrogen sulfate Form-I.

Workup

  1. customSolid material precipitated
  2. stirringThe mixture was stirred at room temperature, for 24 hrs
  3. filtrationIt was filtered
  4. washwashed with methyl tert-butyl ether (30 ml)
  5. customdried at temperature in the range from 30 to 35° C. in a drier

Sources & evidence

ORD record
ord-eefd09b78cf943df86e90ab1f932fc27
Source dataset
uspto-grants-2014_12
Patent number
US08907090B2

Reaction notes

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