Sulfuric Acid → Clopidogrel bisulfate

HRID 1401058Notes

Reaction equation

HRID 1401058 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].[OH:22][S:23]([OH:26])(=[O:25])=[O:24]>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:25][S:23]([OH:26])(=[O:24])=[O:22]

Participants

4

Reactant 2

HCID 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. Dilute H2SO4 was added at 10-15° C. when the solid material precipitated. The reaction mixture was stirred at room temperature, for 24 hrs. Then the mixture was filtered, washed with methyl tert butyl ether (30 ml) and dried at a temperature in the range from 30 to 35° C. in a drier, to get 8 g of Clopidogrel bisulfate salt as crystals. Subsequent analysis confirmed that the crystals were of Clopidogrel hydrogen sulfate Form-I.

Workup

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

Sources & evidence

ORD record
ord-8802cbffff7f4fbf822527f958651368
Source dataset
uspto-grants-2014_12
Patent number
US08907090B2

Reaction notes

Loading…