N-Ethyl-N-benzylaniline → N-benzyl-N-(4-bromophenyl)-N-ethylamine

HRID 897497

Reaction equation

HRID 897497 reaction equation
[CH2:1]([N:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]C1C(=O)C(Br)=CC(Br)(Br)C=1>ClCCl>[CH2:1]([N:8]([C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[CH2:9][CH3:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7098N-Ethyl-N-benzylanilineHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Product 1

HCID 22347350N-benzyl-N-(4-bromophenyl)-N-ethylamineYield 76.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyl-N-phenyl-N-ethylamine (2.25 g, 0.0107 mol) was dissolved in anhydrous dichloromethane (80 mL) and 2,4,4,6-tetrabromocyclohexadiene-1-one (4.36 g, 0.0107 mol) was added in 6 equal portions over a 20 min. period. Stirring was continued at ambient temperature for 20 hours; the organic phase was successively washed with 0.5N solution of sodium hydroxide in water (50 mL), 1N solution of sodium hydroxide in water (50 mL), water (70 mL) and brine (75 mL). The organic phase was dried with magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica using ethyl acetate/n-heptane (1:99) as mobile phase to yield N-benzyl-N-(4-bromophenyl)-N-ethylamine (2.38 g, 0.0082 mol) as a colorless oil.

Workup

  1. washthe organic phase was successively washed with 0.5N solution of sodium hydroxide in water (50 mL), 1N solution of sodium hydroxide in water (50 mL), water (70 mL) and brine (75 mL)
  2. dry with materialThe organic phase was dried with magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-b0d99dd9e1a740b486e15cd5d2e4a1de
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Linked notes

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