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

HRID 585454Notes

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.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]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:31]6[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]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: 85 °C

Procedure

To a mixture of 7-(2-chloroethoxy)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazole (0.412 g, 1.13 mmol) in dry DMF (10 mL) is added N-methyl piperazine (0.125 mL, 1.13 mmol), sodium iodide (0.17 g, 1.13 mmol), and potassium carbonate (0.312 g, 2.26 mmol). The mixture is heated at 85° C. for 20 h. The mixture is then cooled and partitioned between water and CH2Cl2. The organic layer is separated and washed twice with water (200 mL), dried over anhydrous sodium sulfate and concentrated. Column chromatography (50 mL silica) using CH3OH/CH2Cl2 (8/92) with 2 drops per 100 mL of NH4OH gave 0.156 g (32%) of 2-(4-methyl-1-piperazinyl)ethyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether; mp 57° C.

Workup

temperatureThe mixture is then cooled
custompartitioned between water and CH2Cl2
customThe organic layer is separated
washwashed twice with water (200 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-12581df453e34d16aa5d5ab39406e902
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06932961B1

Reaction notes

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