Ethyl Acetate → 4,6,6a,8,9,10a-Hexahydro-10a-methyl-7-(2-phenoxyethyl)-7H-indolo[3,4-gh][1.4]benzoxazine

HRID 129235Notes

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(=O)([O-])[O-].[K+].[K+].I[CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(OCC)(=O)C>CN(C=O)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]([CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:5][CH2:6][O:7]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 4,6,6a,8,9,10a-hexahydro-10a-methyl-7H-indolo[3,4-gh][1.4]benzoxazine (85 mg, 0.37 mmol) in DMF (5 ml) were added potassium carbonate (255 mg, 1.9 mmol) and 1-iodo-2-phenoxyethane (99 mg, 0.4 mmol). The mixture was heated at 60° C for 24 hours. After completion of the reaction, the reaction mixture was added to a mixture of ice water and 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, and the residue was subjected to a silica gel column chromatography, eluting with n-hexane-ethyl acetate (2:1), to afford 59 mg (46%) of the title compound as an amorphous crystalline product.

Workup

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

Sources & evidence

ORD record: ord-ad9a8e3735d6468eb043dfbcd8ad185e
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05466689

Reaction notes

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