Sodium Iodide → HCID 9849326, compound

HRID 2415828Notes

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.[C:27]([O:31][C:32]([N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)=[O:33])([CH3:30])([CH3:29])[CH3:28].[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:37]6[CH2:36][CH2:35][N:34]([C:32]([O:31][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:33])[CH2:39][CH2:38]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 (0.453 g, 1.24 mmol) in dry DMF (6 mL) is added tert-butyl-1-piperazinecarboxylate (0.232 g, 1.24 mmol), sodium iodide (0.018 g, 0.124 mmol), and potassium carbonate (0.342 g, 2.48 mmol). The mixture is heated at 85° C. for 20 h. The mixture is then cooled and partitioned between Et2O and water. The organic layer is washed twice with water (200 mL), dried over anhydrous sodium sulfate and concentrated. Column chromatography (50 mL silica) using CH2Cl2/CH3OH (98/2) yielded 0.487 g (76%) of tert-butyl 4-{2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethyl}-1-peperazinecarboxylate; mp 72° C.;.

Workup

temperatureThe mixture is then cooled
custompartitioned between Et2O and water
washThe organic layer is washed twice with water (200 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated
customyielded 0.487 g (76%) of tert-butyl 4-{2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethyl}-1-peperazinecarboxylate

Sources & evidence

ORD record: ord-9ae8023452fe442783712e8365577b78
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821970B2

Reaction notes

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