Triethylamine → 2-(Benzyl-(3-furylmethyl)amino)ethanol

HRID 2301100Notes

Reaction equation

HRID 2301100 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:14]=[CH:13][O:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Br[CH2:23][CH2:24][OH:25].C(OCC)(=O)C>CN(C)C=O>[CH2:1]([N:8]([CH2:9][C:10]1[CH:14]=[CH:13][O:12][CH:11]=1)[CH2:23][CH2:24][OH:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 108982-BromoethanolHCID 18377394Benzyl(furan-3-ylmethyl)amine

Product 1

HCID 183774232-(Benzyl-(3-furylmethyl)amino)ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Benzyl-3-furylmethylamine (12 g, 64 mmol), triethylamine (18 ml, 130 mmol) and 2-bromoethanol (8.0 g, 64 mmol) were stirred at 60° C. to 70° C. for 16 hours in anhydrous N,N-dimethylformamide (120 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous magnesium sulfate. The solvent was removed by evaporation from the organic layer under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 7.1 g (31 mmol, 48% in yield) of the title compound.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customThe solvent was removed by evaporation from the organic layer under a reduced pressure
  4. customthe thus obtained material was separated
  5. custompurified by a silica gel column chromatography
  6. customto obtain

Sources & evidence

ORD record
ord-492bd57bee044340b7ea1bb8239a774b
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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