1,1-Dichloroethane → Clopidogrel

HRID 1866757Notes

Reaction equation

HRID 1866757 reaction equation
Cl.[S:2]1[C:10]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=2[CH:4]=[CH:3]1.[C:11](=[O:14])([O-])[O-:12].[Na+].[Na+].C(O[C:21]1(Br)[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]1[Cl:28])(=O)C.Cl[CH:31](Cl)C>O>[CH3:31][O:12][C:11]([C@@H:27]([N:7]1[CH2:6][C:5]2[CH:4]=[CH:3][S:2][C:10]=2[CH2:9][CH2:8]1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:21][C:22]=1[Cl:28])=[O:14]

Participants

6

Reactant 4

HCID 63651,1-DichloroethaneHCID 10340Sodium CarbonateHCID 101763424,5,6,7-Tetrahydrothieno(3,2-c)pyridinium chlorideHCID 131727823HCID 131727823, compound

Product 1

HCID 60606Clopidogrel

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

50 gm. of 4,5,6,7-tetrahydrothieno(3,2-c)pyridine hydrochloride was charged in 1 liter reaction vessel containing 500 ml. water and 75.4 gm. sodium carbonate and stirred for 1 hour. 75 gm. of methyl-1-bromo-(2-chlorophenyl) acetate in 250 ml. dichloroethane was added, stirred at 25° C. for 8 hours. The organic layer was separated and washed with water, and distilled the dichloroethane to obtain Clopidogrel base as an oil.

Workup

  1. additioncontaining 500 ml
  2. customThe organic layer was separated
  3. washwashed with water
  4. distillationdistilled the dichloroethane

Sources & evidence

ORD record
ord-e8b4827a21f2401a904515b5411ad34f
Source dataset
uspto-grants-2009_12
Patent number
US07629465B2

Reaction notes

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