Ethanolamine → Ethanol, 2-(phenethylamino)-

HRID 899140Notes

Reaction equation

HRID 899140 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]1([CH:11](Br)[CH3:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>>[CH2:12]([NH:4][CH2:3][CH2:1][OH:2])[CH2:11][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 11454(1-Bromoethyl)benzene

Product 1

HCID 17826Ethanol, 2-(phenethylamino)-Yield 56%

Conditions

Temperature
120 °C

Procedure

A mixture of ethanolamine (10 g, 0.162 mol) and 1-phenylethyl bromide (5 g, 0.027 mol) was stirred at 120° C. for 3 h. The reaction mixture was partitioned between water and dichloromethane. Organic layer was washed with water and brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane to afford (2.5 g) of desired product as a solid.

Workup

  1. customThe reaction mixture was partitioned between water and dichloromethane
  2. washOrganic layer was washed with water and brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography over silica gel using 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-16e3d581b4de45cb974131d6e9d7eb20
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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