Reaction #90934

Reaction equation

1,5-dicyanopentane

NaH

→

2-aminocyclohex-1-enecarbonitrile

Yield 42.5%

Solvents

toluene

toluene

Conditions

Workup

1. 1
   TemperatureThe resulting mixture was refluxed for 4 h
2. 2
   OtherThe reaction mixture was quenched with ethanol (2 mL), water (20 mL) and acetic acid (2 mL)
3. 3
   OtherThe organic layer was separated
4. 4
   Extractionaqueous layer was extracted with ethyl acetate (3×20 mL)
5. 5
   WashThe combined organic layer was washed with brine
6. 6
   Dryingdried over anhydrous Na2SO4
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   workup.ADDITIONWater was added to the crude residue
9. 9
   Filtrationfiltered
10. 10
    Washwashed with hexane

Procedure

To cold toluene (20 mL) was added 60% NaH (720 mg, 18.0 mmol) slowly and followed by a solution of 1,5-dicyanopentane (2.1 mL, 16.37 mmol) in toluene (5 mL) slowly at 0° C. The resulting mixture was refluxed for 4 h and cooled to room temperature. The reaction mixture was quenched with ethanol (2 mL), water (20 mL) and acetic acid (2 mL). The organic layer was separated and aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layer was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. Water was added to the crude residue, then filtered and washed with hexane to afford 850 mg (42%) of 2-aminocyclohex-1-enecarbonitrile (I-7a) as a pale brown solid.

Source