Ethanolamine → HCID 9800447, compound

HRID 585455Notes

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+].[CH2:35]([CH2:37][NH2:38])[OH:36]>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][NH:38][CH2:37][CH2:35][OH:36])=[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 (0.273 g, 0.751 mmol) in dry DMF (10 mL) is added sodium iodide (0.113 g, 0.751 mmol), potassium carbonate (0.207 g, 1.5 mmol), and ethanolamine (0.046 g, 0.751 mmol). The mixture is heated at 85° C. for 17 h. The temperature is then increased to 90° C. and the mixture is allowed to stir for another 5 h. The mixture is then cooled to room temperature and partitioned between water and ether. The organic layer is washed twice with water (50 mL), dried over anhydrous sodium sulfate and concentrated. Column chromatography (50 mL silica gel) using 5% methanol in CH2Cl2 gave 0.123 g (42%) of 2-({2-[(1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl)oxy]ethyl}amino)-1-ethanol.

Workup

temperatureThe temperature is then increased to 90° C.
temperatureThe mixture is then cooled to room temperature
custompartitioned between water and ether
washThe organic layer is washed twice with water (50 mL)
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-b649cc42189449159487e42f72aeb59a
Source dataset: uspto-grants-2005_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06932961B1

Reaction notes

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