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

Temperature

80 °C

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+).

1. temperatureThe mixture was then cooled down to room temperature
2. customstored at that temperature overnight
3. extractionextracted with ether (2×)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was purified by recrystallization from MeOH

ORD record

ord-59996fd215b344649fc9a3bf2832919f

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08541421B2