Homoveratrylamine → HCID 15008971, compound

HRID 465322Notes

Reaction equation

HRID 465322 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+].Cl.ClCCN(CCC1C=C[C:37]([O:40]C)=[C:36](OC)C=1)CCCl>>[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)[CH2:36][CH2:37][OH:40]

Participants

5

Reactant 4

HCID 8421HomoveratrylamineHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 18933201HCID 18933201, compound

Product 1

HCID 15008971HCID 15008971, compoundYield 88%

Procedure

2-(3,4-Dimethoxyphenyl)ethylamine (80.0 g), 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-30499e2134984b57be325dbecf6e3c6d
Source dataset
uspto-grants-1992_10
Patent number
US05153198

Reaction notes

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