Potassium Iodide → 2-((3,4-Dimethoxyphenethyl)(methyl)amino)ethanol

HRID 1106862Notes

Reaction equation

HRID 1106862 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][NH:13][CH3:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].Br[CH2:16][CH2:17][OH:18].[I-].[K+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][C:8]=1[O:9][CH3:10])[CH2:11][CH2:12][N:13]([CH2:16][CH2:17][OH:18])[CH3:14]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 108982-BromoethanolHCID 77039N-Methylhomoveratrylamine

Product 1

HCID 144073182-((3,4-Dimethoxyphenethyl)(methyl)amino)ethanolYield 37.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-(3,4-Dimethoxyphenyl)-N-methylethylamine (2.77 ml, 0.015 mol) and 2-bromoethanol (1.13 ml, 0.015 mol) were dissolved in N,N-dimethylformamide (10 ml). To the resulting solution, potassium iodide (2.45 g, 0.015 mol) was added, followed by stirring at 80° C. for 1.5 h. The reaction mixture was cooled to room temperature and, thereafter the solvent was evaporated under vacuum; after adding a saturated aqueous solution of sodium bicarbonate, three extractions were conducted with ethyl acetate. The organic layers were combined, dried with sodium sulfate and concentrated under vacuum. The residue was purified by being subjected to column chromatography on silica gel using a 9:1 solvent system of chloroform and methanol as an eluent and the fractions containing the end product were collected and the solvent was evaporated under vacuum, followed by drying to yield the end compound 2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethanol (1.35 g) as an oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe solvent was evaporated under vacuum
  3. additionafter adding
  4. extractiona saturated aqueous solution of sodium bicarbonate, three extractions
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified
  8. additionthe fractions containing the end product
  9. customwere collected
  10. customthe solvent was evaporated under vacuum
  11. customby drying

Sources & evidence

ORD record
ord-ca10af87355c46d194c955e99b2c40d1
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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