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

HRID 2352907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2352907
[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-3257c1e6565c49c3aa76e0c7790617f9
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07749530B2

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