Sodium Iodide → HCID 10928314, compound

HRID 1383460Notes

Reaction equation

HRID 1383460 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:21][CH2:22][N:23]1[C:27](=[O:28])[C:26]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:25]2[C:24]1=[O:33].[C:34]([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC(=O)CC>[CH:7]([N:8]1[CH2:9][CH2:10][N:11]([CH2:34][CH2:21][CH2:22][N:23]2[C:27](=[O:28])[C:26]3[C:25](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:24]2=[O:33])[CH2:12][CH2:13]1)([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 70048Benzhydrylpiperazine

Product 1

HCID 10928314HCID 10928314, compoundYield 110%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The mixture of 1-(diphenylmethyl)piperazine (505 mg, 2 mmol, 1.0 eq.), N-(2-bromoethyl)phthalimide (508 mg, 2 mmol, 1.0 eq.), K2CO3 (415 g, 3 mmol, 1.5 eq.), and NaI (420 g, 2.8 mmol, 1.4 eq.) in 2-butanone (10 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 (3×10 ml), then dried over anhydrous Na2SO4. After removed all solvent, the crude product 2-[3-(4-benzhydryl-piperazin-1-yl)-propyl]-isoindole-1,3-dione was yielded (935 mg, 110% yield).

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 (3×10 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. customAfter removed all solvent

Sources & evidence

ORD record
ord-c61d5241f8d445abb4be459274625568
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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