Potassium Carbonate → 2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]isoindole-1,3-dione

HRID 704873Notes

Reaction equation

HRID 704873 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]1=[O:16].[N:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+]>>[N:17]1[CH:22]=[CH:21][CH:20]=[N:19][C:18]=1[N:23]1[CH2:28][CH2:27][N:26]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]2[C:14](=[O:15])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]2=[O:16])[CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 887471-(2-Pyrimidinyl)piperazineHCID 93575N-(4-Bromobutyl)phthalimide

Product 1

HCID 104065392-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]isoindole-1,3-dioneYield 96%

Procedure

0.2 mol of 2-(4-bromobutyl)isoindole-1,3(2H)dione and 0.2 mol of 1-(2-pyrimidyl)piperazine are stirred with 0.2 mol of K2CO3 at 120°-130° C. under an atmosphere of N2 overnight. The mixture is then evaporated to dryness. Water is added and the residue is taken up in methylene chloride. After drying the organic solution, it is evaporated to obtain an oil which crystallises on trituration with cyclohexane. Yield: 96% of theory; melting point=138° C.

Workup

  1. customThe mixture is then evaporated to dryness
  2. additionWater is added
  3. customAfter drying the organic solution, it
  4. customis evaporated
  5. customto obtain an oil which
  6. customcrystallises on trituration with cyclohexane

Sources & evidence

ORD record
ord-ba3982bdaafc48caaabd2ffb8aa54bfa
Source dataset
uspto-grants-1991_01
Patent number
US04988809

Reaction notes

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