Sulfuric Acid → Clopidogrel bisulfate

HRID 1401056Notes

Reaction equation

HRID 1401056 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)CCCCCC>[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 8129HeptanolSolvent

Conditions

Temperature
27.5 °C

Procedure

Clopidogrel base (50 gms) was dissolved in n-heptanol (154 mL) with stirring at 25 to 30° C. and dilute H2SO4 was added at 10-15° C. The reaction mixture was seeded with form-I crystal at 20-25° C. The reaction mixture was stirred at room temperature, for 20-24 hrs, filtered, washed with methyl tert-butyl ether (50 ml) and dried at temperature in the range from 30 to 35° C. in a drier, to get 50 g of Clopidogrel bisulfate salt as crystals. Subsequent analysis confirmed that the crystals were Clopidogrel hydrogen sulfate Form-I.

Workup

  1. customwas seeded with form-I crystal at 20-25° C
  2. stirringThe reaction mixture was stirred at room temperature, for 20-24 hrs
  3. filtrationfiltered
  4. washwashed with methyl tert-butyl ether (50 ml)
  5. customdried at temperature in the range from 30 to 35° C. in a drier

Sources & evidence

ORD record
ord-a1f4a4d0f2cd44b5bb0ef545852355de
Source dataset
uspto-grants-2014_12
Patent number
US08907090B2

Reaction notes

Loading…