Ethanol → HCID 15008971, compound

HRID 1534090Notes

Reaction equation

HRID 1534090 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH2:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH2:15][CH2:16][OH:17].C(=O)([O-])[O-].[K+].[K+].[CH2:24]([OH:26])[CH3:25]>>[OH:17][CH2:16][CH2:15][N:13]([CH2:12][CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:25][CH2:24][OH:26]

Participants

5

Reactant 4

HCID 702EthanolHCID 8421HomoveratrylamineHCID 108982-BromoethanolHCID 11430Potassium Carbonate

Product 1

HCID 15008971HCID 15008971, compoundYield 88%

Procedure

2-(3,4-Dimethoxyphenyl)ethylamine (80.0g), 2-bromoethanol (182 g) and potassium carbonate (201 g) were added to ethanol (1 () and the mixture was refluxed for 16 hours. After cooling, the mixture was filtered and the filtrate was concentrated in vacuo. The oily residue was dissolved in chloroform. The solution was washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated in vacuo to give 104.5 g(88% ) of N,N-bis(2-hydroxyethyl)-2-(3,4-dimethoxyphenyl)ethylamine in oily form.

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionThe oily residue was dissolved in chloroform
  6. washThe solution was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f1afaf13f57432a82ca5ace559f63fa
Source dataset
uspto-grants-1992_02
Patent number
US05087627

Reaction notes

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