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

HRID 1012134Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1012134
[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

Komponenten

4

Edukt 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholine

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-1948c158d8bb4af5a32448986e7bfc9e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977477B2

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