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

HRID 585462Notes

Reaction equation

HRID 585462 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-2385cd9ba68540e5af294e76add1d989
Source dataset
uspto-grants-2005_08
Patent number
US06932961B1

Reaction notes

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