Sodium hydride → N-[4-{4-(4-Fluorobenzoyl)piperidinyl}-2-hydroxybutyl]cyclohexane-1,2-dicarboximide

HRID 1709165

反応式

HRID 1709165 の反応式
[H-].[Na+].[CH:3]12[C:11](=[O:12])[NH:10][C:9](=[O:13])[CH:4]1[CH2:5][CH2:6][CH2:7][CH2:8]2.[O:14]1[CH2:33][CH:15]1[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:20][CH2:19]1>CN(C)C=O>[F:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([CH:21]2[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][CH:15]([OH:14])[CH2:33][N:10]3[C:9](=[O:13])[CH:4]4[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]4[C:11]3=[O:12])[CH2:23][CH2:22]2)=[O:32])=[CH:30][CH:29]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 735591H-Isoindole-1,3(2H)-dione, hexahydro-HCID 157132321-(3,4-Epoxybutyl)-4-(4-fluorobenzoyl)piperidine

生成物 1

HCID 14392396N-[4-{4-(4-Fluorobenzoyl)piperidinyl}-2-hydroxybutyl]cyclohexane-1,2-dicarboximide収率 10.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a mixture of 60% sodium hydride (0.26 g) and dimethylformamide (20 ml), cyclohexane-1,2-dicarboximide (1.13 g) was gradually added. A mixture of 1-(3,4-epoxybutyl)-4-(4-fluorobenzoyl)piperidine (1.7 g) and dimethylformamide (50 ml) was dropwise added thereto at room temperature, and the resultant mixture was kept at an inner temperature of 90° to 100° C. for 3 hours. Insoluble materials were removed by filtration, and the filtrate was distilled to eliminate dimethylformamide. The residue was dissolved in chloroform, washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the objective compound (0.27 g). Yield, 10.2%. M.P., 129°-130° C.

後処理

  1. additionwas gradually added
  2. additionwas dropwise added
  3. customInsoluble materials were removed by filtration
  4. distillationthe filtrate was distilled
  5. dissolutionThe residue was dissolved in chloroform
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-b618c30a073143039ea9f64afa842829
出典データセット
uspto-grants-1990_08
特許番号
US04948799

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