Sodium Iodide → 4,6,6a,8,9,10a-Hexahydro-10a-methyl-7-(4-phthalimidobutyl)-7H-indolo[3,4-gh][1.4]benzoxazine

HRID 129234Notes

Reaction equation

HRID 129234 reaction equation
[CH3:1][C:2]12[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[NH:16][CH:17]=[C:9]([C:10]=34)[CH2:8][CH:3]1[NH:4][CH2:5][CH2:6][O:7]2.[C:18](=[O:21])([O-])[O-].[K+].[K+].[I-].[Na+].[CH3:26][N:27]([CH:29]=[O:30])C>>[CH3:1][C:2]12[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]4[NH:16][CH:17]=[C:9]([C:10]=34)[CH2:8][CH:3]1[N:4]([CH2:12][CH2:13][CH2:14][CH2:26][N:27]1[C:29](=[O:30])[C:3]3=[CH:8][CH:9]=[CH:10][CH:11]=[C:2]3[C:18]1=[O:21])[CH2:5][CH2:6][O:7]2

Participants

5

Reactant 4

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 193727784,6,6a,8,9,10a-Hexahydro-10a-methylindolo[3,4-gh][1.4]benzoxazine

Product 1

HCID 193728054,6,6a,8,9,10a-Hexahydro-10a-methyl-7-(4-phthalimidobutyl)-7H-indolo[3,4-gh][1.4]benzoxazineYield 69%

Conditions

Temperature
60 °C

Procedure

To a solution of 4,6,6a,8,9,10a-hexahydro-10a-methylindolo[3,4-gh][1.4]benzoxazine (100 mg, 0.44 mmol) in DMF (5 ml) were added potassium carbonate (303 mg, 2.2 mmol), N-(4=bromobutyl)phthalimido (124 mg, 0.44 mmol) and sodium iodide (0.66 mg, 0.44 mmol). The mixture was heated at 60° C. for 24 hours. After completion of the reaction, the reaction mixture was added to ice water-ethyl acetate. The organic layer was separated, washed with a saturated aqueous saline solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was subjected to a silica gel column chromatography, eluting with n-hexane-ethyl acetate (3:2), to afford 130 mg (69%) of the title compound as an amorphous crystalline product.

Workup

  1. customAfter completion of the reaction
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous saline solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. washeluting with n-hexane-ethyl acetate (3:2)

Sources & evidence

ORD record
ord-304c28a8bc6a42c381f24f234f86fc89
Source dataset
uspto-grants-1995_11
Patent number
US05466689

Reaction notes

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