Sodium Iodide → Tert-butyl 4-(2-(1,3-dioxoisoindolin-2-YL)ethyl)piperazine-1-carboxylate

HRID 1070769Notes

Reaction equation

HRID 1070769 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:15][CH2:16][N:17]1[C:21](=[O:22])[C:20]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:27].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(CC)=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:15][CH2:16][N:17]2[C:18](=[O:27])[C:19]3[C:20](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:21]2=[O:22])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 22397705Tert-butyl 4-(2-(1,3-dioxoisoindolin-2-YL)ethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

44.7 g (240 mmol) N-(tert-butoxycarbonyl)-piperazine, 60.9 g (240 mmol) N-(2-bromoethyl)-phthalimide, 49.8 g (360 mmol) potassium carbonate and 49.5 g (330 mmol) sodium iodide are heated in 1000 ml ethyl methyl ketone for five hours under reflux. After cooling the reaction mixture and concentrated under vacuum. The residue is taken up in 700 ml chloroform and extracted twice by shaking each with 50 ml water. The organic phase is dried over sodium sulfate and the solvent is distilled off. The residue is crystallized from 110 ml methanol. Colorless crystals of MP. 136-138° C.: Yield 47.6 g (55%).

Workup

  1. temperatureunder reflux
  2. temperatureAfter cooling the reaction mixture
  3. concentrationconcentrated under vacuum
  4. extractionextracted twice
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. distillationthe solvent is distilled off
  7. customThe residue is crystallized from 110 ml methanol
  8. customColorless crystals of MP. 136-138° C.

Sources & evidence

ORD record
ord-c5d800022478415a94ad21c4232ad0e8
Source dataset
uspto-grants-2005_06
Patent number
US06903118B1

Reaction notes

Loading…