Heptanedinitrile → 2-Aminocyclohex-1-ene-1-carbonitrile
Reaction equation
[C:1](#[N:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]#[N:8].CC([O-])(C)C.[K+]>O>[NH2:8][C:7]1[CH2:6][CH2:5][CH2:4][CH2:3][C:2]=1[C:1]#[N:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
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) δ1.58-1.71 (m, 4H), 2.12-2.20 (m, 4H), 4.23 (bs, 2H). MS 123 (MH+).