N-Methyl-N-phenylbenzylamine → N-benzyl-N-(4-bromophenyl)-N-methylamine

HRID 432205

Reaction equation

HRID 432205 reaction equation
[CH2:1]([N:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]C1C(=O)C(Br)=CC(Br)(Br)C=1>ClCCl>[CH2:1]([N:8]([C:10]1[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=1)[CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69191N-Methyl-N-phenylbenzylamineHCID 884332,4,4,6-Tetrabromocyclohexa-2,5-dienone

Product 1

HCID 22347392N-benzyl-N-(4-bromophenyl)-N-methylamineYield 56.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyl-N-phenyl-N-methylamine (4.41 g, 0.0224 mol) was dissolved in anhydrous dichloromethane (150 mL) and 2,4,4,6-tetrabromocyclohexadiene-1-one(9.16 g, 0.0224 mol) was added in 10 equal portions over a 30 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 (100 mL), 1N solution of sodium hydroxide in water (100 mL), water (120 mL) and brine (120 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-methylamine (3.52 g, 0.0127 mol) as a colorless oil.

Workup

  1. washThe organic phase was successively washed with 0.5N solution of sodium hydroxide in water (100 mL), 1N solution of sodium hydroxide in water (100 mL), water (120 mL) and brine (120 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-b4d0e4dee0fc4432b379558712d568b2
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Linked notes

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