Sulfuric Acid → Clopidogrel

HRID 1866754Notes

Reaction equation

HRID 1866754 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].S(=O)(=O)(O)O>C(OCC)(=O)C>[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].[S:21]1[C:16]2[CH2:15][CH2:14][NH:13][CH2:18][C:17]=2[CH:19]=[CH:20]1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 60606Clopidogrel

Product 2

HCID 60606ClopidogrelHCID 30850764,5,6,7-Tetrahydrothieno(3,2-c)pyridine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
10 °C

Procedure

In yet another aspect, Form II of clopidogrel is prepared from ethyl acetate at a lower temperature of 5° to 15° C. comprising the steps of dissolving (+) clopidogrel base in ethyl acetate at 25° to 30° C., cool to 5° to 15° C. and mixing with conc. sulphuric acid at the said temperature, maintaining the mass under stirring for a period of 8 to 10 hours at 5 to 15° C. to yield crystals of clopidogrel Form II. The crystals obtained are filtered and dried and is identified as Form II by PXRD, FTIR and DSC without detectable contamination of Form I.

Workup

  1. customat 25° to 30° C.
  2. temperaturecool to 5° to 15° C.
  3. temperaturemaintaining the mass

Sources & evidence

ORD record
ord-57118af0b2e34adeb80de807c7025096
Source dataset
uspto-grants-2009_12
Patent number
US07629465B2

Reaction notes

Loading…