Hydrazine hydrate (1:1) → 4-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamine

HRID 640975Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 640975
[N+:1]([C:4]1[CH:18]=[CH:17][C:7]([CH2:8][NH:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:6][CH:5]=1)([O-])=O.O.NN>CCO.[Ni]>[N:12]1([CH2:11][CH2:10][NH:9][CH2:8][C:7]2[CH:6]=[CH:5][C:4]([NH2:1])=[CH:18][CH:17]=2)[CH2:13][CH2:14][CH2:15][CH2:16]1

Komponenten

5

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 28654092N-[(4-Nitrophenyl)methyl]-2-(pyrrolidin-1-yl)ethan-1-amine

Produkt 1

HCID 686996624-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamineAusbeute 75,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

The (4-Nitro-benzyl)-(2-pyrrolidin-1-yl-ethyl)-amine (0.503 g, 2.02 mmol) was dissolved in EtOH (10 mL) under Ar(g), and hydrazine hydrate (0.439 mL, 14.14 mmol) was added. Subsequently, excess RaNi was added in dropwise until the solution stopped bubbling. The suspension was then allowed to stir for an additional 45 minutes at 65° C. The suspension was cooled to r.t. and then filtered over celite. The celite was washed with MeOH and the combined organic solutions were then concentrated in vacuo affording a pure 4-[(2-Pyrrolidin-1-yl-ethylamino)-methyl]-phenylamine as a light purple oil (0.331 g, 1.52 mmol, 75% yield).

Aufarbeitung

  1. additionwas added
  2. customstopped bubbling
  3. temperatureThe suspension was cooled to r.t.
  4. filtrationfiltered over celite
  5. washThe celite was washed with MeOH
  6. concentrationthe combined organic solutions were then concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a8b9c2873a414781a41b0cc0cd9dfd72
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07692005B2

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