Diethanolamine → HCID 11770129, compound

HRID 1928537Notes

Reaction equation

HRID 1928537 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][OH:7].Br[CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:1][CH2:2][CH2:3][N:4]([CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5][CH2:6][OH:7]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-

Product 1

HCID 11770129HCID 11770129, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The reaction mixture of 2-(2-hydroxy-ethylamino)ethanol (32 g, 310 mmol), 1-(2-bromoethoxy)benzene (51 g, 256 mmol), and potassium carbonate (70 g, 512 mmol) in ethanol (200 mL) was refluxed overnight, concentrated, and partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated. The residue was purified by column chromatography to afford the title compound (45 g, 78%).

Workup

  1. temperaturewas refluxed overnight
  2. concentrationconcentrated
  3. custompartitioned between water and ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-ce6f958296a34e70b8b597c0f29faa50
Source dataset
uspto-grants-2012_05
Patent number
US08183374B2

Reaction notes

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