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

HRID 353991

Reaktionsgleichung

Reaktionsgleichung von HRID 353991
[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-70aaa5cdd28c41ae874829a47aea108a
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06756391B2

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