Acetyl chloride → (2R)-4-acetyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl) piperazine

HRID 1379197

Reaction equation

HRID 1379197 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@H:9]1[CH2:14][C:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[NH:17][CH:16]=1)=[O:7].C(=O)([O-])[O-].[K+].[K+].[C:39](Cl)(=[O:41])[CH3:40]>CN(C)C=O>[C:39]([N:11]1[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]2[CH:4]=[C:3]([C:2]([F:1])([F:31])[F:32])[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=2)[C@H:9]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH2:10]1)(=[O:41])[CH3:40]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 10972505(2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-ylmethyl)piperazine

Product 1

HCID 86751297(2R)-4-acetyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl) piperazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred mixture of (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (0.15 g) and potassium carbonate (0.14 g) in dimethylformamide (10 ml) was added acetyl chloride (0.04 ml) at room temperature. After being stirred for 3 hours, the reaction mixture was quenched with water (50 ml) and extracted with dichloromethane (50 ml). The organic layer was washed with aqueous sodium bicarbonate solution and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified on a silica gel column (10 g) eluting with a mixture of dichloromethane and methanol (20:1). The fractions containing object compound were collected and evaporated under reduced pressure. To the resulting oily product was added a mixed solvent of ethyl ether and diisopropyl ether, and the mixture was concentrated under reduced pressure. The obtained powder was collected by filtration and dried in vacuo to give (2R)-4-acetyl-1-[3,5-bis(trifluoromethyl)benzoyl]-2-(1H-indol-3-yl-methyl)piperazine (0.09 g) as a powder.

Workup

  1. customthe reaction mixture was quenched with water (50 ml)
  2. extractionextracted with dichloromethane (50 ml)
  3. washThe organic layer was washed with aqueous sodium bicarbonate solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified on a silica gel column (10 g)
  7. washeluting with a mixture of dichloromethane and methanol (20:1)
  8. additionThe fractions containing object compound
  9. customwere collected
  10. customevaporated under reduced pressure
  11. additionTo the resulting oily product was added a mixed solvent of ethyl ether and diisopropyl ether
  12. concentrationthe mixture was concentrated under reduced pressure
  13. filtrationThe obtained powder was collected by filtration
  14. customdried in vacuo

Sources & evidence

ORD record
ord-a3bfa9d9d24a4237a11e995e5ecf47fc
Source dataset
uspto-grants-1997_09
Patent number
US05670505

Linked notes

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