Benzylethanolamine → N-Benzyl-N-(2-hydroxyethyl)acetamide

HRID 899159Notes

Reaction equation

HRID 899159 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[CH2:5]([NH:12][CH2:13][CH2:14][OH:15])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C>ClCCl>[CH2:5]([N:12]([CH2:13][CH2:14][OH:15])[C:1](=[O:3])[CH3:2])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 4348BenzylethanolamineHCID 6367Acetyl chlorideHCID 8471Triethylamine

Product 1

HCID 24284454N-Benzyl-N-(2-hydroxyethyl)acetamideYield 35.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.858 g, 10.8 mmol) was added drop by drop to a solution of N-benzyl ethanol amine (1.5 g, 9.9 mmol) and triethylamine (1.5 g, 14.9 mmol) in dry dichloromethane (20 ml) at 0° C. under nitrogen atmosphere and stirred at room temperature overnight. The reaction was quenched with water and extracted with dichloromethane. The organic layer was washed with water, 10% aq. NaHCO3, brine and dried over sodium sulfate. Solvent evaporation under reduced pressure, followed by column chromatography over silica gel using 5% methanol in dichloromethane as eluent afforded 0.68 g of the desired product as an oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water, 10% aq. NaHCO3, brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporation under reduced pressure

Sources & evidence

ORD record
ord-70b14efc50ee40d98e6d237ef0e0e69d
Source dataset
uspto-grants-2008_04
Patent number
US07354917B2

Reaction notes

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