Adiponitrile → HCID 11790115, compound

HRID 1886140Notes

Reaction equation

HRID 1886140 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([NH2:7])[CH2:5][CH3:6].[C:8](#N)[CH2:9][CH2:10][CH2:11][CH2:12][C:13]#[N:14].[H][H]>[Ni]>[C:13]([CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[NH:7][CH:4]([CH2:5][CH3:6])[CH2:3][CH2:2][NH:1]1)#[N:14]

Participants

5

Reactant 3

HCID 8128AdiponitrileHCID 1024441,3-Pentanediamine2×HCID 178418361HCID 178418361, compound

Product 1

HCID 11790115HCID 11790115, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Conditions

Temperature
90 °C

Procedure

Fifty grams of 1,3-diaminopentane (99%, 0.485 mole), 116 g (1.07 moles) adiponitrile and 2.3 g Raney® nickel were charged to a 300 cc autoclave reactor. The mixture was stirred and heated at 90° C. and 650 psig hydrogen pressure for 10 hours. The mixture was cooled and filtered under nitrogen. Capillary GC analysis of the filtered product indicated a 56% conversion of 1,3-diaminopentane and 59% yield of 2-(4-cyanobutyl)-4-ethylhexahydropyrimidine.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered under nitrogen

Sources & evidence

ORD record
ord-f780b039d0d64d7ca86d84d7c92cf120
Source dataset
uspto-grants-1992_09
Patent number
US05149809

Reaction notes

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