Water → N-(3-bromobenzyl)acetamide

HRID 1059218Notes

Reaction equation

HRID 1059218 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH2:7].[C:11](OC(=O)C)(=[O:13])[CH3:12].O.C(OCC)(=O)C>N1C=CC=CC=1>[Br:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:7][C:11](=[O:13])[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 27249803-Bromobenzylamine hydrochloride

Product 1

HCID 12175281N-(3-bromobenzyl)acetamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-bromobenzylamine hydrochloride (5.20 g) in pyridine (30 ml) was added acetic anhydride (3.2 ml) at 0° C. and the mixture was stirred at room temperature for 24 h. Water and ethyl acetate were added to the reaction mixture for partitioning, and the organic layer was washed with 1N hydrochloric acid, aqueous sodium hydrogen carbonate and brine, dried (magnesium sulfate) and concentrated under reduced pressure. The residue was recrystallized from hexane-ethyl acetate to give the title compound (4.00 g) as colorless needle crystals.

Workup

  1. customfor partitioning
  2. washthe organic layer was washed with 1N hydrochloric acid, aqueous sodium hydrogen carbonate and brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-35cf1564147845648b941737314ce4d1
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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