4-(3,4-Dinitrobenzyl)morpholine → 4-(Morpholinomethyl)benzene-1,2-diamine

HRID 1012134ノート

反応式

HRID 1012134 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][C:16]=1[N+:17]([O-])=O)[CH2:7][N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)([O-])=O>[Fe].O1CCOCC1.O>[N:8]1([CH2:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:16]([NH2:17])=[CH:15][CH:14]=2)[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1

参加物

4

反応物 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholine

生成物 1

HCID 251933094-(Morpholinomethyl)benzene-1,2-diamine収率 73%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 218864351,4-Dioxane--water (1/1)溶媒

実験手順

To a mixture of 4-(3,4-dinitro-benzyl)-morpholine (2.5 g, 9.3 mmol), Fe powder (5.2 g, 93 mmol) and FeSO4.7H2O (1.3 g, 4.6 mmol) was added 1,4-dioxane:water (5:1, 60 ml). The mixture was refluxed for 3 h, filtered through celite, washing with MeOH, and reduced in vacuo azeotroping with toluene. EtOAc (100 ml) was added and insoluble material removed via filtration. The filtrate was reduced in vacuo to give 4-morpholin-4-ylmethyl-benzene-1,2-diamine as a dark brown solid (1.4 g, 73%). (LC/MS: Rt 0.40, no ionization).

後処理

  1. temperatureThe mixture was refluxed for 3 h
  2. filtrationfiltered through celite
  3. washwashing with MeOH
  4. customazeotroping with toluene
  5. additionEtOAc (100 ml) was added
  6. custominsoluble material removed via filtration

出典と根拠

ORDレコード
ord-1948c158d8bb4af5a32448986e7bfc9e
出典データセット
uspto-grants-2011_07
特許番号
US07977477B2

反応ノート

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