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

HRID 1093891

반응식

HRID 1093891 반응식
[C:1]([C:3]1[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH:4]=1)#[CH:2].Cl[CH2:11][CH2:12][CH2:13][NH:14][CH2:15][CH2:16][CH3:17].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.O>[CH2:13]([N:14]1[CH2:15][CH2:16][CH2:17][C:1]([C:3]2[CH2:8][CH2:7][CH2:6][C:5](=[O:9])[CH:4]=2)=[CH:2]1)[CH2:12][CH3:11]

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 145707953-Ethynylcyclohex-2-en-1-oneHCID 222458383-Chloro-N-propyl-1-propanamine

생성물 1

HCID 222458393-(1-Propyl-1,4,5,6-tetrahydro-pyridin-3-yl)-cyclohex-2-enone

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

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).

후처리

  1. temperaturethe mixture was refluxed under N2 for 10 h
  2. temperatureAfter cooling the mixture
  3. extractionextracted with dichloromethane (3×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe resulting dark oil was purified by column chromatography (silica, ethyl acetate)
  8. customto give a yellow red oil

출처 및 근거

ORD 기록
ord-affada35f5b74efabdc44829bbc12c9d
출처 데이터셋
uspto-grants-2012_03
특허 번호
USRE043244E1

연결된 노트

불러오는 중…