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

HRID 1379197

반응식

HRID 1379197 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a3bfa9d9d24a4237a11e995e5ecf47fc
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05670505

연결된 노트

불러오는 중…