Sodium Iodide → HCID 9801794, compound

HRID 1279718Notes

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.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[NH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>CN(C=O)C>[N:35]1([CH2:2][CH2:3][O:4][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]3[C:17]=2[C:16]2[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]34)[CH:13]=[CH:14][CH:15]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of 7-(2-chloroethoxy)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazole (0.28 g, 0.769 mmol) in dry DMF (6 mL) is added sodium iodide (0.09 g, 0.6 mmol), potassium carbonate (0.207 g, 1.5 mmol), and piperidine (0.13 g, 1.5 mmol). The mixture is heated at 70° C. for 6 h and then at room temperature for 18 h. The mixture is then partitioned between water and ether. The ether layer is washed three times with water (80 mL). The organic layer is dried over sodium sulfate and concentrated. Column chromatography (50 mL) silica gel using 1% methanol in CH2C2 as eluent gave 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl 2-(1-piperidinyl)ethyl ether (TLC: acetone/hexane, 20/80, Rf=0.42) which is converted to the methanesulfonate salt to give 0.134 g (34%) of 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl 2-(1-piperidinyl)ethyl ether.

Workup

customThe mixture is then partitioned between water and ether
washThe ether layer is washed three times with water (80 mL)
dry with materialThe organic layer is dried over sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-c7ab285c90e84cb581b3a6efdcd93172
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06448397B1

Reaction notes

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