Reacción #1747827

Ecuación de reacción

3-Ethynyl-cyclohex-2-enone

(3-Chloro-propyl)-propyl-amine

Cs2CO3

→

3-(1-Propyl-1,4,5,6-tetrahydro-pyridin-3-yl)-cyclohex-2-enone

Disolventes

acetonitril

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture was refluxed under N2 for 10 h
2. 2
   TemperaturaAfter cooling the mixture
3. 3
   Extracciónextracted with dichloromethane (3×50 mL)
4. 4
   LavadoThe combined organic layers were washed with brine
5. 5
   Secadodried (MgSO4)
6. 6
   Otroevaporated
7. 7
   OtroThe resulting dark oil was purified by column chromatography (silica, ethyl acetate)
8. 8
   Otroto give a yellow red oil

Procedimiento

3-Ethynyl-cyclohex-2-enone (3.20 g, 26.8 mmol) (from a) above) and (3-Chloro-propyl)-propyl-amine (4.50 g, 33.2 mmol) were mixed in acetonitril (50 mL). Cs2CO3 (100 mg) and KI (200 mg) were added and the mixture was refluxed under N2 for 10 h. After cooling the mixture was diluted with water (50 mL) and extracted with dichloromethane (3×50 mL). The combined organic layers were washed with brine, dried (MgSO4) and evaporated. The resulting dark oil was purified by column chromatography (silica, ethyl acetate) to give a yellow red oil. Yield 5.1 g, 23.3 mmol (87%). IR (neat) 2932, 2871, 1589, 1538, 1157 cm−1; 1H-NMR (CDCl3) δ 6.84 (s, 1H), 5.69 (s, 1H), 3.04-3.12 (m, 4H), 2.44 (t, 2H), 2.33 (t, 2H), 2.18 (t, 2H), 1.83-2.03 (m, 4H), 1.49-1.64 (m, 2H), 0.87 (t, 3H) ppm; 13C-NMR (CDCl3) δ 197.0, 158.5, 140.1, 112.1, 102.4, 56.6, 44.3, 35.6, 23.6, 21.4, 20.2, 20.1, 19.7, 9.6 ppm; MS (CI) m/z 220 (M+1).

Fuente