Water → N-(2-phenylethyl)acetamide

HRID 1749496Notes

Reaction equation

HRID 1749496 reaction equation
[C:1]1([CH2:7][CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10](Cl)(=[O:12])[CH3:11].O>C(Cl)Cl>[CH2:8]([NH:9][C:10](=[O:12])[CH3:11])[CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1001PhenethylamineHCID 6367Acetyl chloride

Product 1

HCID 70143N-(2-phenylethyl)acetamideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-phenylethanamine (5.00 g, 41.32 mmol) and TEA (6.26 g, 61.98 mmol) in anhydrous DCM (50 mL) was added dropwise acetyl chloride (3.57 g, 45.45 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 30 min. Water was added and the mixture was extracted with DCM. The combined organic layers were washed with saturated aqueous ammonium chloride, brine and concentrated to give the title product as a yellow oil (6.06 g, 37.19 mmol, 90% yield). MS (ESI) m/z 164.1 [M+H]+.

Workup

  1. customThe resulting reaction mixture
  2. extractionthe mixture was extracted with DCM
  3. washThe combined organic layers were washed with saturated aqueous ammonium chloride, brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-fc56bd11626041659889806566ef0e0d
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

Loading…