Cesium carbonate → 1-(4,6-Dimethyl-pyridin-2-yl)-4-(2-methyl-4-nitro-phenyl)-piperazine

HRID 37862

反応式

HRID 37862 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[CH3:17].[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[N:22]=[C:21]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:20]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][C:19]1[CH:24]=[C:23]([CH3:25])[N:22]=[C:21]([N:26]2[CH2:27][CH2:28][N:29]([C:8]3[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=3[CH3:17])[CH2:30][CH2:31]2)[CH:20]=1

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 83315Benzene, 1-chloro-2-methyl-4-nitro-HCID 233680631-(4,6-Dimethylpyridin-2-YL)piperazine

生成物 1

HCID 668515241-(4,6-Dimethyl-pyridin-2-yl)-4-(2-methyl-4-nitro-phenyl)-piperazine収率 27.1%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒2 回

実験手順

Caesium carbonate (10.19 g, 31.38 mmol), 1-chloro-2-methyl-4-nitro-benzene (0.98 g, 5.75 mmol) and 1-(4,6-dimethyl-pyridin-2-yl)-piperazine (1.0 g, 5.23 mmol) were taken in toluene (35 mL) and degassed with argon for 15 min. A slurry of 2-dicyclophosphino-2′-(N,N-dimethylamino)-biphenyl (0.2 g, 0.52 mmol) and palladium acetate (0.116 g, 0.52 mmol) in toluene (5 mL) was added, the mixture degassed for another 10 min and then heated at reflux for 16 h. The mixture was cooled to room temperature and filtered, washing with ethyl acetate. The filtrate was washed with 2N hydrochloric acid, water, and brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to obtain the crude compound. Purification by column chromatography over silica gel (100-200 mesh) using 0-12% ethyl acetate in petroleum ether as eluent gave 1-(4,6-dimethyl-pyridin-2-yl)-4-(2-methyl-4-nitro-phenyl)-piperazine (0.463 g, 27%) as a solid.

後処理

  1. customdegassed with argon for 15 min
  2. customthe mixture degassed for another 10 min
  3. temperatureheated
  4. temperatureat reflux for 16 h
  5. filtrationfiltered
  6. washwashing with ethyl acetate
  7. washThe filtrate was washed with 2N hydrochloric acid, water, and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customto obtain the crude compound
  12. customPurification by column chromatography over silica gel (100-200 mesh)

出典と根拠

ORDレコード
ord-1dcc0993a9df45538c543723262d88fe
出典データセット
uspto-grants-2013_09
特許番号
US08524705B2

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