Sodium Carbonate → Phthalimide

HRID 846052Notes

Reaction equation

HRID 846052 reaction equation
FC(F)(F)C1N=C(N2CCNCC2)C=CC=1.BrCC[N:20]1[C:24](=[O:25])[C:23]2=[CH:26][CH:27]=[CH:28][CH:29]=[C:22]2[C:21]1=[O:30].C(=O)([O-])[O-].[Na+].[Na+]>>[C:21]1(=[O:30])[C:22]2[C:23](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](=[O:25])[NH:20]1

Participants

4

Reactant 3

HCID 10340Sodium CarbonateHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 114247401-[6-(Trifluoromethyl)pyridin-2-yl]piperazine

Product 1

HCID 6809PhthalimideYield 33%

Procedure

A mixture of 69.3 g of 1-[6-(trifluoromethyl) -2-pyridinyl]piperazine, and 129.6 g of N-(2-bromo-ethyl)phthalimide and 57.2 g of sodium carbonate is heated at reflux for 23 hours. The resulting precipitate is filtered off and the ethanol evaporated. The concentrate is dissolved in dichloromethane, washed with water, dried over magnesium sulfate, and evaporated. The resulting precipitate is recrystallized from isopropanol to give 39.5 g of 2-μ-[4-[6-(trifluoromethyl)-2-pyridinyl]-1-piperazinyl]ethyl]-1H-isoindole-1,3-dione (yield 33%).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 23 hours
  3. filtrationThe resulting precipitate is filtered off
  4. customthe ethanol evaporated
  5. dissolutionThe concentrate is dissolved in dichloromethane
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe resulting precipitate is recrystallized from isopropanol

Sources & evidence

ORD record
ord-bc13360904ee4f8bbecca02d45dd1f82
Source dataset
uspto-grants-1992_08
Patent number
US05135931

Reaction notes

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