1-Phenylpiperazine → 2-[2-(4-Phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione

HRID 1984125ノート

反応式

HRID 1984125 の反応式
[C:1]1([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32].CCCCCC>CN(C=O)C.O.CCOC(C)=O>[C:1]1([N:7]2[CH2:12][CH2:11][N:10]([CH2:20][CH2:21][N:22]3[C:23](=[O:32])[C:24]4[C:25](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26]3=[O:27])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

8

反応物 4

HCID 70961-PhenylpiperazineHCID 8058HexaneHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium Carbonate

生成物 1

HCID 85979842-[2-(4-Phenylpiperazin-1-yl)ethyl]isoindole-1,3-dione収率 55.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

4-phenylpiperazine (4.50 g, 27.74 mmol) was dissolved in 30 ml DMF, then K2CO3 (11.50 g, 83.21 mmol) and N-(2-bromoethyl)phthalimide (8.46 g, 33.28 mmol) were added thereto and stirred at about 80° C. The reaction progress and completion were confirmed using TLC (hexane:EtOAc=1:1). Upon completion of the reaction, water was added to the reaction mixture and then was extracted with CH2Cl2. The organic layer was dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The concentrate was separated by column chromatography (hexane:EtOAc:CH2Cl2=3:1:2) to obtain the titled compound.

後処理

  1. additionwas added to the reaction mixture
  2. extractionwas extracted with CH2Cl2
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe concentrate was separated by column chromatography (hexane:EtOAc:CH2Cl2=3:1:2)

出典と根拠

ORDレコード
ord-aadba0a2ee324c9e90d36da4cbef783b
出典データセット
uspto-grants-2009_06
特許番号
US07544686B2

反応ノート

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