Sodium hydride → HCID 14576386, compound

HRID 2108001Notes

Reaction equation

HRID 2108001 reaction equation
[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[CH2:34][CH:15]1[CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][CH:21]([C:24]2[C:28]3[CH:29]=[CH:30][C:31]([F:33])=[CH:32][C:27]=3[O:26][N:25]=2)[CH2:20][CH2:19]1>CN(C)C=O>[F:33][C:31]1[CH:30]=[CH:29][C:28]2[C:24]([CH:21]3[CH2:22][CH2:23][N:18]([CH2:17][CH2:16][CH:15]([OH:14])[CH2:34][N:10]4[C:9](=[O:13])[CH:4]5[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]5[C:11]4=[O:12])[CH2:19][CH2:20]3)=[N:25][O:26][C:27]=2[CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 735591H-Isoindole-1,3(2H)-dione, hexahydro-HCID 14576385HCID 14576385, compound

Product 1

HCID 14576386HCID 14576386, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 60% sodium hydride (0.12 g) and dimethylformamide (5 ml), cyclohexane-1,2-dicarboximide (0.5 g) was portionwise added. A solution of 1-(3,4-epoxybutyl)-4-(6-fluoro-1,2-benzisoxazol-3-yl)piperidine (0.8 g) in dimethylformamide (10 ml) was dropwise added thereto at room temperature, and the resultant mixture was kept at an inner temperature of 90 to 100° C. for 16.5 hours. Insoluble materials were removed by filtration, and the residue was combined with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The resulting crude crystals were recrystallized from a mixture of isopropyl ether and isopropanol to give the objective compound (0.6 g).

Workup

  1. additionwas portionwise added
  2. customInsoluble materials were removed by filtration
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting crude crystals were recrystallized from a mixture of isopropyl ether and isopropanol

Sources & evidence

ORD record
ord-74929d15930e409c9f5e16930ccbd9d0
Source dataset
uspto-grants-1990_06
Patent number
US04937249

Reaction notes

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