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

HRID 1984125Notes

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-aadba0a2ee324c9e90d36da4cbef783b
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07544686B2

Reaction notes

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