Heptanedinitrile → 2-Aminocyclohex-1-ene-1-carbonitrile

HRID 366399Notes

Reaction equation

HRID 366399 reaction equation
[C:1]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[N:9])#[N:2].[H-].[Na+]>O>[NH2:2][C:1]1[CH2:3][CH2:4][CH2:5][CH2:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 2

HCID 12590HeptanedinitrileHCID 24758Sodium hydride

Product 1

HCID 2901752-Aminocyclohex-1-ene-1-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,5-Dicyanopentane (Aldrich Chemicals) (25.0 g, 205 mmol), sodium hydride (60% oil dispersion; 8.2 g, 205 mmol) and T.H.F. (150 ml) were heated under reflux for 17 hours. After cooling, water (150 ml) was added and the upper organic layer removed, dried (Na2SO4) filtered and the solvent evaporated. Recrystallisation from hot toluene (80° C.) gave the product as beige crystals.

Workup

  1. temperature(150 ml) were heated
  2. temperatureunder reflux for 17 hours
  3. temperatureAfter cooling
  4. customthe upper organic layer removed
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent evaporated
  8. customRecrystallisation from hot toluene (80° C.)

Sources & evidence

ORD record
ord-c54ede75b2ad4a5c849208ca430985ff
Source dataset
uspto-grants-2000_10
Patent number
US06130228

Reaction notes

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