1,3-Benzenediacetonitrile → 2-[3-(2-Aminoethyl)phenyl]ethanamine

HRID 1372836

Reaktionsgleichung

Reaktionsgleichung von HRID 1372836
[C:1]1([CH2:10][C:11]#[N:12])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]#[N:9])[CH:2]=1>CO.[Ni]>[C:3]1([CH2:7][CH2:8][NH2:9])[CH:4]=[CH:5][CH:6]=[C:1]([CH2:10][CH2:11][NH2:12])[CH:2]=1

Komponenten

4

Edukt 1

HCID 693751,3-Benzenediacetonitrile

Produkt 1

HCID 27496402-[3-(2-Aminoethyl)phenyl]ethanamineAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1,3-phenylenediacetonitrile (9.37 g, 60 mmol) in CH3OH (saturated with NH3, 150 mL) was added Raney-Ni (ca. 20 g, previously washed with CH3OH several times) and the mixture was hydrogenated at 45 psi on a Parr apparatus for 48 h. The reaction mixture was filtered through celite and the filtrate evaporated to give the crude product (9.45 g, 96%) as a light green oil: 1H NMR (CDCl3) δ 0.80–1.50 (br s, 4H), 2.70–2.76 (m, 4H), 2.94–2.99 (m, 4H), 7.01–7.07 (m, 3H), 7.18–7.26 (m, 1H). This was used in the next step without further purification.

Aufarbeitung

  1. washpreviously washed with CH3OH several times) and the mixture
  2. filtrationThe reaction mixture was filtered through celite
  3. customthe filtrate evaporated

Quellen und Nachweise

ORD-Eintrag
ord-67fe9fa7508247699b225773adde4033
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07160872B2

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