Phenethylamine → 2-Chloro-N-phenethyl-acetamide

HRID 1045645Notes

Reaction equation

HRID 1045645 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[C:6]1([CH2:12][CH2:13][NH2:14])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:1][CH2:2][C:3]([NH:14][CH2:13][CH2:12][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 1001PhenethylamineHCID 6577Chloroacetyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 949212-Chloro-N-phenethyl-acetamideYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetylchloride (13.55 g, 120 mmol) was dropped into a solution of 2-phenylethylamine (12.12 g, 100 mmol), sodium bicarbonate (10.6 g, 126 mmol) in dichloromethane (100 ml) under ice cooling and the mixture was stirred for 2 hours. After addition of ice-water, the organic layer was separated and washed with 1N hydrochloric acid and brine. The solvents were removed under reduced pressure and the residue was recrystallized from mixture of water (20 ml) and methanol (30 ml) to afford 2-chloro-N-phenethyl-acetamide (18.33 g, 93%).

Workup

  1. customthe organic layer was separated
  2. washwashed with 1N hydrochloric acid and brine
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was recrystallized from mixture of water (20 ml) and methanol (30 ml)

Sources & evidence

ORD record
ord-cdd68044ea2b476f86677bb84ebdeb8d
Source dataset
uspto-grants-2013_10
Patent number
US08569294B2

Reaction notes

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