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

HRID 2219113

Reaction equation

HRID 2219113 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-2be0558de9314b8a91ece7d704e2cdb2
Source dataset
uspto-grants-2008_08
Patent number
US07414065B2

Linked notes

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