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

HRID 1709165

반응식

HRID 1709165 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b618c30a073143039ea9f64afa842829
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04948799

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