Sodium Iodide → 2-(3-(4-(5-Chloro-2-methylphenyl)piperazin-1-yl)propyl)isoindoline-1,3-dione

HRID 2407066Notes

Reaction equation

HRID 2407066 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:15].[Na+].[I-].[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:31])=[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=1>CC(C)=O>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([CH3:31])=[C:23]([N:25]2[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][CH2:4][N:5]3[C:13](=[O:14])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=4)[C:6]3=[O:15])[CH2:29][CH2:30]2)[CH:24]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 21611N-3-BromopropylphthalimideHCID 693767N-(5-Chloro-2-methylphenyl)piperazine

Product 1

HCID 585388742-(3-(4-(5-Chloro-2-methylphenyl)piperazin-1-yl)propyl)isoindoline-1,3-dioneYield 81%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(3-bromopropyl)isoindoline-1,3-dione (2.68 g, 10 mmol) and NaI (20 mmol) in acetone was refluxed for 5 h, then to it was added 1-(5-chloro-2-methylphenyl)piperazine (2.11 g, 10.0 mmol). The reflux was continued for 12 h. Reaction was then cooled to room temperature, filtered through celite and concentrated.. The crude product was recrystalized from acetone to give the title compound as a white solid (3.21 g. 81%).

Workup

  1. temperaturewas refluxed for 5 h
  2. customReaction
  3. filtrationfiltered through celite and
  4. concentrationconcentrated
  5. customThe crude product was recrystalized from acetone

Sources & evidence

ORD record
ord-a1e8fa82c09547ca91ee61dbf0709d62
Source dataset
uspto-grants-2014_08
Patent number
US08809530B1

Reaction notes

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