N-Methylbenzylamine → 2-(N-benzyl-N-methylamino)-1-(2-furyl)ethanol

HRID 544517Notes

Reaction equation

HRID 544517 reaction equation
Br[CH2:2][C:3]([C:5]1[O:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[CH3:10][NH:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:12]([N:11]([CH2:2][CH:3]([C:5]1[O:6][CH:7]=[CH:8][CH:9]=1)[OH:4])[CH3:10])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7669N-MethylbenzylamineHCID 11430Potassium CarbonateHCID 27950762-Bromo-1-(furan-2-yl)ethan-1-one

Product 1

HCID 133172512-(N-benzyl-N-methylamino)-1-(2-furyl)ethanolYield 68.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-(Bromoacetyl)furan (95 g) is added slowly to a stirred mixture of 75 g of N-methylbenzylamine and 70 g of potassium carbonate in 300 ml of methanol at 20°-30° C. The mixture is stirred at room temperature for 2.5 hours, and the insoluble matter is filtered off. To the filtrate is added 20 g of sodium borohydride at 10°-20° C. with stirring, and the mixture is stirred at room temperature for 3 hours. The solvent is then distilled off under reduced pressure, water is added to the residue, and the separated oil is extracted with ethyl acetate. The extract is washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Distillation of the residue gives 80 g of 2-(N-benzyl-N-methylamino)-1-(2-furyl)ethanol as pale yellow viscous oil, boiling at 130°-138° C. (0.2 mmHg).

Workup

  1. filtrationthe insoluble matter is filtered off
  2. additionTo the filtrate is added 20 g of sodium borohydride at 10°-20° C.
  3. stirringwith stirring
  4. stirringthe mixture is stirred at room temperature for 3 hours
  5. distillationThe solvent is then distilled off under reduced pressure, water
  6. additionis added to the residue
  7. extractionthe separated oil is extracted with ethyl acetate
  8. washThe extract is washed with water
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. distillationDistillation of the residue

Sources & evidence

ORD record
ord-6f9134d21a2f493cae0b3a9f72c341c1
Source dataset
uspto-grants-1984_05
Patent number
US04450165

Reaction notes

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