Water → 2-(2-(4-(2,3-Dichlorophenyl)piperazin-1-yl)ethyl)isoindoline-1,3-dione

HRID 1626300Notes

Reaction equation

HRID 1626300 reaction equation
Cl.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][N:25]1[C:33](=[O:34])[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]1=[O:35].O>CN(C=O)C>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[N:10]1[CH2:15][CH2:14][N:13]([CH2:23][CH2:24][N:25]2[C:26](=[O:35])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]2=[O:34])[CH2:12][CH2:11]1

Participants

6

Reactant 4

HCID 962WaterHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 116303721-(2,3-Dichlorophenyl)piperazine hydrochloride

Product 1

HCID 583588142-(2-(4-(2,3-Dichlorophenyl)piperazin-1-yl)ethyl)isoindoline-1,3-dioneYield 81.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-(2,3-Dichlorophenyl)piperazine hydrochloride (3.16 g, 11.8 mmol) and potassium carbonate (4.08 g, 29.5 mmol) were added to the solution of 2-(2-bromoethyl)isoindoline-1,3-dione (3 g, 11.8 mmol) in DMF (20 ml). The resulting reaction mixture was stirred for overnight at room temperature. After reaction complete, water (40 ml) was added thereto and then normal work-up was taken. The residue thus obtained was purified with normal phase preparative column to afford the title compound (3.87 g, 81% yield) as white solid.

Workup

  1. customThe resulting reaction mixture
  2. customAfter reaction complete
  3. customThe residue thus obtained
  4. customwas purified with normal phase preparative column

Sources & evidence

ORD record
ord-cd4b0015aad24ae6823c540ca7469095
Source dataset
uspto-grants-2014_07
Patent number
US08785453B2

Reaction notes

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