Ethanolamine → Benzylethanolamine

HRID 899137Notes

Reaction equation

HRID 899137 reaction equation
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:9]([CH2:11][NH2:12])[OH:10]>[Cl-].[Na+].O>[CH2:1]([NH:12][CH2:11][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 7498Benzyl Bromide

Product 1

HCID 4348BenzylethanolamineYield 91%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of benzyl bromide (15 g, 0.0872 mol) and ethanol amine (26.5 g, 0.436 mol) was stirred at 120° C. for 3 h. The reaction mixture was diluted with brine and extracted with dichloromethane. The organic layer was washed with water and brine and dried over sodium sulfate. Solvent evaporated under reduced pressure and the residue was purified by column chromatography over silica gel using 4% methanol in dichloromethane as eluent to give N-benzyl ethanolamine (12 g) as a liquid.

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. customSolvent evaporated under reduced pressure
  5. customthe residue was purified by column chromatography over silica gel using 4% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-ac581095862548e9aa80109cf449d278
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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