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

HRID 1596233ノート

反応式

HRID 1596233 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-774f2a7ce9534c7dbaad8de8ca3bab03
出典データセット
uspto-grants-2001_09
特許番号
US06291464B1

反応ノート

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