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

HRID 353991Notes

Reaction equation

HRID 353991 reaction equation
[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

Participants

4

Reactant 1

HCID 693751,3-Benzenediacetonitrile

Product 1

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

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-70aaa5cdd28c41ae874829a47aea108a
Source dataset
uspto-grants-2004_06
Patent number
US06756391B2

Reaction notes

Loading…