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

HRID 50648

反応式

HRID 50648 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-126b512605ac405ea8a83500c878b631
出典データセット
uspto-grants-2004_03
特許番号
US06713479B2

関連ノート

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