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

HRID 1012134노트

반응식

HRID 1012134 반응식
[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

참가 물질

4

반응물 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholine

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-1948c158d8bb4af5a32448986e7bfc9e
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07977477B2

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