Sodium Iodide → 2-(4-Morpholinyl)ethyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether

HRID 2415831Notes

Reaction equation

Cl[CH2:2][CH2:3][O:4][C:5]1[C:17]2[C:16]3[C:11]4=[C:12]([O:18][CH2:19][CH:20]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[N:10]4[C:9]=2[CH:8]=[CH:7][CH:6]=1)[CH:13]=[CH:14][CH:15]=3.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:21]1([CH:20]2[N:10]3[C:11]4[C:16]([C:17]5[C:5]([O:4][CH2:3][CH2:2][N:27]6[CH2:32][CH2:31][O:30][CH2:29][CH2:28]6)=[CH:6][CH:7]=[CH:8][C:9]=53)=[CH:15][CH:14]=[CH:13][C:12]=4[O:18][CH2:19]2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 7-(2-chloroethoxy)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazole (0.278 g, 0.764 mmol) in dry DMF (10 mL) is added morpholine (0.133 g, 1.53 mmol), sodium iodide (0.114 g, 0.764 mmol), and potassium carbonate (0.211 g, 1.53 mmol). The mixture is heated to 100° C. for 6 h. The mixture is removed from heat and stirred at room temperature for three days. The mixture is then partitioned between water and Et2O. The layers are separated and the organic layer is washed twice with water (50 mL) and then dried over anhydrous sodium sulfate and concentrated. Column chromatography (50 mL silica) using CH2Cl2/acetone/hexanes (7:2:1) gave 0.192 g (61%) of 2-(4-morpholinyl)ethyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether.

Workup

customThe mixture is removed
temperaturefrom heat
customThe mixture is then partitioned between water and Et2O
customThe layers are separated
washthe organic layer is washed twice with water (50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-c15e2d5cc8104b7dac53305139b50ae8
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821970B2

Reaction notes

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