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

HRID 576505Notes

Reaction equation

HRID 576505 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 recrystallized 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
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from acetone

Sources & evidence

ORD record
ord-23c411aacfc14b86ba59836a7cfc6d95
Source dataset
uspto-grants-2015_05
Patent number
US09040508B2

Reaction notes

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