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

HRID 1193991

Reaktionsgleichung

Reaktionsgleichung von HRID 1193991
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 14392396N-[4-{4-(4-Fluorobenzoyl)piperidinyl}-2-hydroxybutyl]cyclohexane-1,2-dicarboximideAusbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-712387d672ad406ba84d39ce571ab966
Quelldatensatz
uspto-grants-1989_03
Patentnummer
US04812461

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