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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence