Hydrazine hydrate (1:1) → N1-(2-morpholinoethyl)benzene-1,4-diamine

HRID 640986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640986
[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.O.NN>[Ni].CCO>[N:1]1([CH2:7][CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 21975017N-(2-Morpholinoethyl)-4-nitroaniline

Produkt 1

HCID 21974995N1-(2-morpholinoethyl)benzene-1,4-diamineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A 50 mL round bottom flask was charged with (2-Morpholin-4-yl-ethyl)-(4-nitro-phenyl)-amine (0.315 g, 1.26 mmol) and EtOH (5 mL). Hydrazine Hydrate (0.278 mL, 8.82 mmol) was then added to the solution. Excess RaNi was then added in dropwise until gas evolution ceased. The suspension was then allowed to stir for an additional 1 h at 65° C. The suspension was cooled to room temperature and then was filtered over celite. The celite was washed with MeOH (˜20 mL) and the combined organic solutions were then concentrated in vacuo affording pure N-(2-Morpholin-4-yl-ethyl)-benzene-1,4-diamine as a light purple oil (0.220 g, 0.995 mmol, 79% yield).

Aufarbeitung

  1. temperatureThe suspension was cooled to room temperature
  2. filtrationwas filtered over celite
  3. washThe celite was washed with MeOH (˜20 mL)
  4. concentrationthe combined organic solutions were then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-62f02ee0bc62407483c6c832985201ab
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692005B2

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