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

HRID 640989Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640989
[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 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-2f65560b35624e60b901a5e11da990d8
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692005B2

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