تفاعل #1747827

معادلة التفاعل

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

المذيبات

acetonitril

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed under N2 for 10 h
2. 2
   درجة الحرارةAfter cooling the mixture
3. 3
   استخلاصextracted with dichloromethane (3×50 mL)
4. 4
   غسيلThe combined organic layers were washed with brine
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىevaporated
7. 7
   أخرىThe resulting dark oil was purified by column chromatography (silica, ethyl acetate)
8. 8
   أخرىto give a yellow red oil

الإجراء التجريبي

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).

المصدر