Ethanolamine → [(2-{[(1R)-1-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl]oxy}ethyl)amino]ethanol

HRID 2415840Notes

Reaction equation

HRID 2415840 reaction equation
[C:1]1([C@H:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:23][CH2:24][CH2:25]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.[I-].[Na+].C(=O)([O-])[O-:30].[K+].[K+].[CH2:35]([CH2:37][NH2:38])O>CN(C=O)C>[C:1]1([C@H:7]2[N:21]3[C:22]4[C:14]([C:15]5[C:16]([O:23][CH2:24][CH2:25][NH:38][CH:37]([OH:30])[CH3:35])=[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

Participants

6

Reactant 4

HCID 700EthanolamineHCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 121486392-Chloroethyl (1R) 1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether

Product 1

HCID 69796239[(2-{[(1R)-1-Phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl]oxy}ethyl)amino]ethanolYield 24%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a mixture of 2-chloroethyl (1R)-1-phenyl-1,2-dihydro[1,4]oxazino[2,3,4-jk]carbazol-7-yl ether in DMF (20 mL) is added sodium iodide (1.0 g, 6.7 mmol), potassium carbonate (2.0 g, 14.5 mmol), and ethanolamine (0.42 mL, 7.0 mmol). The mixture is heated to 85° C. for 18 h. The mixture then is partitioned between water and CH2Cl2. The layers are separated and the organic layer washed twice with water (200 mL). The organic layer is dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography with silica gel (60 mL) using CH3OH/CH2Cl2 (2/98) and then rechromatographed with CH3OH/CH2Cl2/NH4OH (4/96/0.1) gave 0.62 g (24%) of the title compound.

Workup

  1. customThe mixture then is partitioned between water and CH2Cl2
  2. customThe layers are separated
  3. washthe organic layer washed twice with water (200 mL)
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customrechromatographed with CH3OH/CH2Cl2/NH4OH (4/96/0.1)

Sources & evidence

ORD record
ord-12c5d708f381447e8b49b1f565cd8d7a
Source dataset
uspto-grants-2004_11
Patent number
US06821970B2

Reaction notes

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