Reaction #2487407

Reaction equation

DIEA

Cyclohex-3-enecarboxylic acid

NH2CH2CH2CH3

EDC.HCl

→

N-propylcyclohex-3-enecarboxamide

Yield 55.0%

Solvents

CH2Cl2

Acetone CH2Cl2

Conditions

Procedure

Cyclohex-3-enecarboxylic acid (0.71 mmol, 90 mg), NH2CH2CH2CH3 (0.86 mmol, 70 μL) and EDC.HCl (0.86 mmol, 164 mg) were dissolved in CH2Cl2 (3 mL). DIEA (1.43 mmol, 252 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-propylcyclohex-3-enecarboxamide 26 as a white powder (65 mg, 55%). 1H NMR (400 MHz, CDCl3) δ 5.64 (m, 3H), 3.17 (dd, J=8 Hz, J=8 Hz, 2H), 2.30-1.93 (m, 5H), 1.87-1.81 (m, 1H), 1.72-1.59 (m, 1H), 1.43 (m, 2H), 0.87 (t, J=8 Hz, 3H). 13C NMR (100 MHz, CDCl3) δ 175.93, 126.94, 125.61, 41.52, 41.22, 28.35, 25.97, 24.80, 23.07, 11.49.

Source