1,4-Benzenediacetonitrile → 1,4-Cyclohexanediethanamine

HRID 48387Notes

Reaction equation

HRID 48387 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.[H][H]>[Pt]=O.C(O)(=O)C>[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.[NH2:9][CH2:8][CH2:7][CH:4]1[CH2:5][CH2:6][CH:1]([CH2:10][CH2:11][NH2:12])[CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 693271,4-BenzenediacetonitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 27498872-[4-(2-Aminoethyl)phenyl]ethylamineHCID 140298721,4-CyclohexanediethanamineYield 339.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 176Acetic AcidSolvent

Procedure

Into a 250 mL reduction vessel were placed 1,4-phenylenediacetonitrile (2 g, 12.8 mmol), acetic acid (95 mL), and platinum oxide (0.25 g) and the mixture was heated at 60° C. under 60 psi (413.7 kPa) of hydrogen gas for 6 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)cyclohexyl]ethylamine, (3.7 g, 100%) as an oil. Electron spray M.S. 171 (M*+1).

Workup

  1. customInto 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-40332072034f4f19847166152c9f8905
Source dataset
uspto-grants-2004_03
Patent number
US06703425B2

Reaction notes

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