Ammonia → 2-[4-(2-Aminoethyl)phenyl]ethylamine

HRID 48363Notes

Reaction equation

HRID 48363 reaction equation
[C:1]1([CH2:10][C:11]#[N:12])[CH:6]=[CH:5][C:4]([CH2:7][C:8]#[N:9])=[CH:3][CH:2]=1.N.[H][H]>[Ni].CO>[NH2:9][CH2:8][CH2:7][C:4]1[CH:5]=[CH:6][C:1]([CH2:10][CH2:11][NH2:12])=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 693271,4-BenzenediacetonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 27498872-[4-(2-Aminoethyl)phenyl]ethylamineYield 98%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Scheme I, step B′: Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (10 g, 64.02 mmol), liquid ammonia (25 mL), and W4-W6 range (medium range activity) Raney Nickel (1.25 g) in methanol (125 mL), and the mixture was heated at 100° C. under 300 psi (2068 kPa) of hydrogen gas for 10 hours. The reaction was cooled to room temperature and filtered through a Celite® cake and the filtrate was concentrated under reduced vacuum to give the intermediate title compound, 2-[4-(2-aminoethyl)phenyl]ethylamine, (10.3 g, 98%) as an oil. Electron spray M.S. 165 (M*+H).

Workup

  1. customScheme I, step B′: Into a 250 mL reduction vessel were placed
  2. filtrationfiltered through a Celite® cake
  3. concentrationthe filtrate was concentrated under reduced vacuum

Sources & evidence

ORD record
ord-80862a1fbb344d8d94617c30b01cc0a7
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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