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

HRID 897495

反応式

HRID 897495 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 22347392N-benzyl-N-(4-bromophenyl)-N-methylamine収率 56.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-537f0f3535f241e083af1fac449392d9
出典データセット
uspto-grants-2005_07
特許番号
US06921763B2

関連ノート

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