反応 #1747827

反応方程式

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

溶媒

acetonitril

water

反応条件

後処理

1. 1
   温度the mixture was refluxed under N2 for 10 h
2. 2
   温度After cooling the mixture
3. 3
   抽出extracted with dichloromethane (3×50 mL)
4. 4
   洗浄The combined organic layers were washed with brine
5. 5
   乾燥dried (MgSO4)
6. 6
   その他evaporated
7. 7
   その他The resulting dark oil was purified by column chromatography (silica, ethyl acetate)
8. 8
   その他to give a yellow red oil

実験手順

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).

出典