Sodium Iodide → HCID 21187763, compound

HRID 1383458Notes

Reaction equation

HRID 1383458 reaction equation
Br.[CH:2]([NH:15][CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:23][CH2:24][N:25]1[C:29](=[O:30])[C:28]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:27]2[C:26]1=[O:35].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC(=O)CC>[CH:2]([NH:15][CH:16]1[CH2:21][CH2:20][N:19]([CH2:23][CH2:24][N:25]2[C:26](=[O:35])[C:27]3[C:28](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]2=[O:30])[CH2:18][CH2:17]1)([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 70245335HCID 70245335, compound

Product 1

HCID 21187763HCID 21187763, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The mixture of benzhydryl-piperidin-4-yl-amine hydrogen bromide salt (1.74 g, 5 mmol, 1.0 eq.), N-(2-bromoethyl)phthalimide (1.27 g, 5 mmol, 1.0 eq.), K2CO3 (1.73 g, 12.5 mmol, 2.5 eq.), and NaI (1.05 g, 7.0 mmol, 1.4 eq.) in 2-butanone (20 ml) was refluxed for 2-3 hours. The mixture was then cooled to room temperature. The white solid was filtered off and was washed with small amount of CHCl3. The filtrates were combined and concentrated. The resulted residue was dissolved in CHCl3 (100 ml). The solution was washed with water (3×20 ml), then dried over anhydrous Na2SO4. After removed all solvent, the crude product 2-{2-[4-(benzhydryl-amino)-piperidin-1-yl]-ethyl} -isoindole-1,3-dione was yielded (2.70 g).

Workup

  1. temperaturewas refluxed for 2-3 hours
  2. filtrationThe white solid was filtered off
  3. washwas washed with small amount of CHCl3
  4. concentrationconcentrated
  5. dissolutionThe resulted residue was dissolved in CHCl3 (100 ml)
  6. washThe solution was washed with water (3×20 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. customAfter removed all solvent

Sources & evidence

ORD record
ord-024c91153859407cad07ff94336b5eeb
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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