Dimethylformamide → N-(4-acetyl-1-piperazinyl)-N-benzyl-4-fluorobenzamide

HRID 1596233노트

반응식

HRID 1596233 반응식
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([NH:10][C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CN(C)C=O.[H-].[Na+].[CH2:27](Br)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>O>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([N:10]([CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:11](=[O:19])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 181428FK-960

생성물 1

HCID 21701689N-(4-acetyl-1-piperazinyl)-N-benzyl-4-fluorobenzamide

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

To a stirred mixture of N-(4-acetyl-1-piperazinyl)-4-fluorobenzamide (230 mg) and N,N-dimethylformamide (3 ml) was added sodium hydride (60% oil dispersion, 35 mg) in one portion at 0° C. The mixture was stirred at 0° C. for 1 hour then benzyl bromide (0.17 ml) was added to this mixture at 0° C. After stirring at 0° C. for 1.5 hours, water was added and the solvent was evaporated. The residue was taken up in ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated. The residue was purified by column chromatography eluting with a mixture of methanol and ethyl acetate (1:5) to give crystals. Crystallization from ethyl acetate and n-hexane to give N-(4-acetyl-1-piperazinyl)-N-benzyl-4-fluorobenzamide (260 mg).

후처리

  1. stirringAfter stirring at 0° C. for 1.5 hours
  2. customthe solvent was evaporated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography
  7. washeluting with a mixture of methanol and ethyl acetate (1:5)
  8. customto give crystals
  9. customCrystallization from ethyl acetate and n-hexane

출처 및 근거

ORD 기록
ord-774f2a7ce9534c7dbaad8de8ca3bab03
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06291464B1

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