Ammonium → 1-Acetyl-4-(4-imidazol-1-ylphenyl)-piperazine

HRID 1987755ノート

反応式

HRID 1987755 の反応式
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13](Br)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C1(C=CC(=O)C=CC2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH4+]>C1(C)C(C)=CC=CC=1>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

参加物

8

反応物 6

HCID 223AmmoniumHCID 795ImidazoleHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 95417Dibenzylidene acetoneHCID 138219171-(4-(4-Bromophenyl)piperazin-1-YL)ethanone

生成物 1

HCID 231182961-Acetyl-4-(4-imidazol-1-ylphenyl)-piperazine収率 79.6%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
125 °C

実験手順

To a reaction solution prepared by dissolving 20 g of 1-acetyl-4-(4-bromophenyl)-piperazine and 7.9 g of imidazole in 120 ml of xylene, 16.9 g of 1,10-phenanthroline, 1.4 g of 1,5-diphenyl-1,4-pentadien-3-one, 28.9 g of cesium carbonate and 1.8 g of a copper (I) trifluoromethanesulfonate benzene complex, as a catalyst, were added at room temperature, followed by heating at reflux in an argon gas flow at 125° C. for 24 hours. After the completion of the reaction, the reaction solution was mixed with 300 ml of an aqueous ammonium solution and then extracted with chloroform. The organic layer was washed with saturated saline and then dried over anhydrous magnesium sulfate. After removing magnesium sulfate by filtration and concentrating under reduced pressure, the residue was subjected to silica gel column chromatography (chloroform:ethyl acetate=3:1→chloroform:methanol=20:1) to obtain 15.2 g of the objective 1-acetyl-4-(4-imidazol-1-ylphenyl)-piperazine (melting point: 181-182° C.).

後処理

  1. customTo a reaction solution prepared
  2. additionas a catalyst, were added at room temperature
  3. temperatureby heating
  4. customAfter the completion of the reaction
  5. extractionextracted with chloroform
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customAfter removing magnesium sulfate
  9. filtrationby filtration
  10. concentrationconcentrating under reduced pressure

出典と根拠

ORDレコード
ord-369b446eca72455a8f872d990ce72911
出典データセット
uspto-grants-2009_06
特許番号
US07553837B2

反応ノート

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