1-(2-Methoxyphenyl)piperazine → [1-(4-Chloro-phenyl)-cyclobutyl]-{3-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]piperidin-1-yl}-methanone

HRID 1788072

반응식

HRID 1788072 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20]OS(C)(=O)=O)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[N:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]([N:14]3[CH2:19][CH2:18][CH2:17][CH:16]([CH2:20][N:37]4[CH2:38][CH2:39][N:34]([C:29]5[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=5[O:27][CH3:26])[CH2:35][CH2:36]4)[CH2:15]3)=[O:13])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 13461-(2-Methoxyphenyl)piperazineHCID 8471TriethylamineHCID 12992442Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl ester

생성물 1

HCID 9891394[1-(4-Chloro-phenyl)-cyclobutyl]-{3-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]piperidin-1-yl}-methanone수율 43.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 2 (1.0 g, 2.60 mmol) in acetonitrile (25 mL) was added 1-(2-methoxyphenyl)piperazine (0.55 g, 2.86 mmol) and triethylamine (2 mL). The reaction was stirred and refluxed for 20 h. After cooling to room temperature, most of solvent was removed by rotary evaporation. The reaction mixture was partitioned between dichloromethane and water (50 mL each), and the organic layer was washed with sat. sodium carbonate (50 mL) and water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The organic residue was purified by flash chromatography on silica gel, eluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4) to give 3 (0.54 g, 43%) as a light brown solid; C28H36ClN3O2, LRMS (m/z)=483 (MH+).

후처리

  1. temperaturerefluxed for 20 h
  2. customwas removed by rotary evaporation
  3. customThe reaction mixture was partitioned between dichloromethane and water (50 mL each)
  4. washthe organic layer was washed with sat. sodium carbonate (50 mL) and water
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe organic residue was purified by flash chromatography on silica gel
  9. washeluting with dichloromethane/2.0 M ammonia in ethyl alcohol (96:4)

출처 및 근거

ORD 기록
ord-8f55b5e0e1b34aed9a393af46d3bc746
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07511141B2

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