Sodium Iodide → N,N-Diethyl-N-{3-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]propyl}amine

HRID 2415838Notes

Reaction equation

[C:1]1([CH:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:23][CH2:24][CH2:25][CH2:26]Cl)=[CH:17][CH:18]=[CH:19][C:20]=53)=[CH:13][CH:12]=[CH:11][C:10]=4[O:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:28]([NH:30][CH2:31][CH3:32])[CH3:29].[I-].[Na+]>CN(C=O)C>[CH2:28]([N:30]([CH2:31][CH3:32])[CH2:26][CH2:25][CH2:24][O:23][C:16]1[C:15]2[C:14]3[C:22]4=[C:10]([O:9][CH2:8][CH:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[N:21]4[C:20]=2[CH:19]=[CH:18][CH:17]=1)[CH:11]=[CH:12][CH:13]=3)[CH3:29]

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 3-chloropropyl 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether (0.45 g, 1.2 mmol) in dry DMF (10 mL) is added diethylamine (1.2 mL, 12 mmol) and sodium iodide (0.18 g, 1.2 mmol). The mixture is heated at 50° C. overnight. The mixture is partitioned between water and CH2Cl2. The layers are separated and the organic layer washed with brine (50 mL) followed by water (100 mL). The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography with silica gel (60 mL) using CH3OH/CH2Cl2 (3/97) as eluent gave 0.216 g (43%) of the title compound.

Workup

customThe mixture is partitioned between water and CH2Cl2
customThe layers are separated
washthe organic layer washed with brine (50 mL)
dry with materialThe organic layer is dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-a9431961274f4862bf82a457717e213e
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821970B2

Reaction notes

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