Reaction #2487408

Reaction equation

DIEA

Cyclohex-3-enecarboxylic acid

EDC.HCl

Acetone CH2Cl2

→

N-octylcyclohex-3-enecarboxamide

Yield 82.0%

Solvents

CH2Cl2

Conditions

Procedure

Cyclohex-3-enecarboxylic acid (1.11 mmol, 140 mg), NH2-octyl (1.33 mmol, 220 μL) and EDC.HCl (1.33 mmol, 255 mg) were dissolved in CH2Cl2 (3 mL). DIEA (2.22 mmol, 393 μL) was added at 0° C., and the reaction was stirred for 16 h at rt. The usual workup and chromatography (Acetone/CH2Cl2/10:90) yielded N-octylcyclohex-3-enecarboxamide 27 as a white powder (215 mg, 82%). 1H NMR (400 MHz, CDCl3) δ 5.77 (s, 1H), 5.63 (s, 2H), 3.18 (dd, J=8 Hz, J=8 Hz, 2H), 2.33-2.00 (m, 5H), 1.86-1.82 (s, 1H), 1.70-1.60 (m, 1H), 1.43 (m, 2H), 1.22 (m, 10H), 0.82 (t, J=8 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 175.89, 126.88, 125.59, 41.46, 39.56, 31.91, 29.81, 29.39, 29.33, 28.32, 27.05, 25.93, 24.79, 22.75, 14.19.

Source