반응 #1747827

반응 방정식

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

용매

acetonitril

water

반응 조건

후처리

1. 1
   온도the mixture was refluxed under N2 for 10 h
2. 2
   온도After cooling the mixture
3. 3
   추출extracted with dichloromethane (3×50 mL)
4. 4
   세척The combined organic layers were washed with brine
5. 5
   건조dried (MgSO4)
6. 6
   기타evaporated
7. 7
   기타The resulting dark oil was purified by column chromatography (silica, ethyl acetate)
8. 8
   기타to give a yellow red oil

실험 절차

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).

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