Reaction #798796

Reaction equation

1,7-heptanedinitrile

t-BuOK

→

title compound

Yield 75.0%

2-Aminocyclohex-1-enecarbonitrile

Yield 75.0%

Solvents

water

Conditions

Workup

1. 1
   TemperatureThe mixture was then cooled down to room temperature
2. 2
   Otherstored at that temperature overnight
3. 3
   Extractionextracted with ether (2×)
4. 4
   WashThe combined organic layers were washed with brine
5. 5
   Dryingdried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated
8. 8
   OtherThe residue was purified by recrystallization from MeOH

Procedure

A stirred mixture of 1,7-heptanedinitrile (24.44 g, 0.2 mol) and t-BuOK (22.44 g, 0.2 mol) was heated at 80° C. for 3 h under nitrogen. The mixture was then cooled down to room temperature and stored at that temperature overnight. The residue was treated with water, and extracted with ether (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by recrystallization from MeOH to give the title compound as a white solid (18.2 g, 75%). 1H NMR (400 MHz, CDCl3) δ 1.58-1.71 (m, 4H), 2.12-2.20 (m, 4H), 4.23 (bs, 2H). MS 123 (MH+).

Source