Methyl iodide → N-Methyl-N-phenylbenzylamine

HRID 897494

反応式

HRID 897494 の反応式
[H-].[Na+].[C:3]1([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH3:18]>CN(C)C=O>[CH2:10]([N:9]([CH3:18])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66028Benzylaniline

生成物 1

HCID 69191N-Methyl-N-phenylbenzylamine収率 39.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

60% dispersion of sodium hydride in mineral oil (2.37 g, 0.0592 mol) was added to a solution of N-phenyl-N-benzylamine (10.33 g, 0.0564 mol) in anhydrous N,N-dimethylformamide (200 mL) at 0° C. The reaction mixture was warmed up to ambient temperature and stirred for 45 min. Iodomethane (7.99 g, 0.0564 mol) was added dropwise and the stirring at ambient temperature was continued under an atmosphere of nitrogen for 20 hours. The solvent was removed under reduced pressure and the residue partitioned between ethyl acetate (250 mL) and water (200 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 (2:98) as mobile phase to yield N-benzyl-N-methyl-N-phenylamine (4.4 g, 0.0223 mol) as a yellow oil.

後処理

  1. waitthe stirring at ambient temperature was continued under an atmosphere of nitrogen for 20 hours
  2. customThe solvent was removed under reduced pressure
  3. customthe residue partitioned between ethyl acetate (250 mL) and water (200 mL)
  4. dry with materialThe organic phase was dried with magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica

出典と根拠

ORDレコード
ord-656c75b3de044a41823b9e81847c7ef9
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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