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

HRID 1984125Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984125
[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

Komponenten

8

Edukt 4

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

Produkt 1

HCID 85979842-[2-(4-Phenylpiperazin-1-yl)ethyl]isoindole-1,3-dioneAusbeute 55,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-aadba0a2ee324c9e90d36da4cbef783b
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544686B2

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