Toluene → Bis(4-methoxybenzyl)amine

HRID 59930

反応式

HRID 59930 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH3:11][O:12][C:13]1[CH:20]=[CH:19][C:16]([CH2:17][NH2:18])=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.[BH4-].[Na+]>O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][NH:18][CH2:17][C:16]2[CH:19]=[CH:20][C:13]([O:12][CH3:11])=[CH:14][CH:15]=2)=[CH:3][CH:4]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 312444-MethoxybenzaldehydeHCID 754524-MethoxybenzylamineHCID 4311764Sodium borohydride

生成物 1

HCID 714952Bis(4-methoxybenzyl)amine

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
5 °C

実験手順

p-Anisaldehyde (411 mmol), 4-methoxybenzylamine (411 mmol) and toluene (500 mL) were combined in a round bottomed flask fitted with a condenser and a Dean-Stark trap. The reaction was refluxed for 1 h during which water was removed from the reaction mixture. The reaction was cooled and concentrated. The residue was dissolved in MeOH (120 mL). The mixture was cooled to 5° C. and NaBH4 (205 mmol) was added in portions over 45 min. The reaction was slowly heated to reflux. After 2 h at reflux, the reaction was cooled to room temperature and concentrated. The residue was dissolved in EtOAc. The organic layer was washed (3×H2O and brine), dried (Na2SO4) and concentrated to yield the desired product.

後処理

  1. customfitted with a condenser
  2. customwas removed from the reaction mixture
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated
  5. dissolutionThe residue was dissolved in MeOH (120 mL)
  6. temperatureThe reaction was slowly heated to reflux
  7. temperatureAfter 2 h at reflux
  8. temperaturethe reaction was cooled to room temperature
  9. concentrationconcentrated
  10. dissolutionThe residue was dissolved in EtOAc
  11. washThe organic layer was washed (3×H2O and brine)
  12. dry with materialdried (Na2SO4)
  13. concentrationconcentrated

出典と根拠

ORDレコード
ord-2781ce35c46f4b819672aab6953c86b7
出典データセット
uspto-grants-2016_09
特許番号
US09440929B2

関連ノート

読み込み中…