Hydrazine hydrate (1:1) → N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamine

HRID 2352921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2352921
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:6][CH:5]=1)([O-])=O.O.NN>[Ni].CCO>[N:13]1([CH2:12][CH2:11][NH:10][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 585989084-Nitro-N-[2-(pyrrolidin-1-yl)ethyl]aniline

Produkt 1

HCID 16090620N~1~-[2-(Pyrrolidin-1-yl)ethyl]benzene-1,4-diamineAusbeute 71,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

A 25 mL round bottom flask was charged with (4-Nitro-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine (0.352 g, 1.50 mmol) and EtOH (5 mL). Hydrazine Hydrate (0.326 mL, 10.5 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-Pyrrolidin-1-yl-ethyl)-benzene-1,4-diamine as a light purple oil (0.219 g, 1.07 mmol, 71% 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-ff493131027c4f50af2cb86586f39394
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749530B2

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