Reaction #54285

Reaction equation

2,2-Dimethylhex-1-ylamine

methyl iodide

sodium amide

capronitrile

→

2,2-dimethylcapronitrile

Yield 81.0%

Solvents

water

toluene

toluene

Conditions

Workup

1. 1
   Temperaturereflux
2. 2
   workup.ADDITIONAfter addition
3. 3
   Temperaturerefluxed for an additional 2 hr
4. 4
   Temperatureperiod, cooled
5. 5
   workup.ADDITIONtreated with 150 ml
6. 6
   OtherThe organic layer is separated
7. 7
   Washwashed with water
8. 8
   Dryingdried over magnesium sulfate
9. 9
   workup.DISTILLATIONConcentration of the dried solution under reduced pressure and distillation of residual material

Procedure

2,2-Dimethylhex-1-ylamine--A solution of capronitrile (25 g., 0.26 mole) and methyl iodide (75 g., 0.53 Mole) in 80 ml. of dry toluene is warmed to 80° and treated gradually with a suspension of sodium amide (25.4 g., 0.65 mole) in 100 ml. of toluene at a rate sufficient to maintain general reflux. After addition is complete, the mixture is stirred and refluxed for an additional 2 hr. period, cooled and treated with 150 ml. of water. The organic layer is separated, washed with water and dried over magnesium sulfate. Concentration of the dried solution under reduced pressure and distillation of residual material affords an 81% yield of 2,2-dimethylcapronitrile.

Source