Sodium Iodide → 2-[2-(4-Benzhydrylsulfanyl-piperidin-1-yl)-ethyl]-isoindole-1,3-dione

HRID 1383463Notes

Reaction equation

HRID 1383463 reaction equation
[CH:1]([S:14][CH:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:22][CH2:23][N:24]1[C:28](=[O:29])[C:27]2=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]2[C:25]1=[O:34].C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CC(=O)CC>[CH:1]([S:14][CH:15]1[CH2:20][CH2:19][N:18]([CH2:22][CH2:23][N:24]2[C:25](=[O:34])[C:26]3[C:27](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:28]2=[O:29])[CH2:17][CH2:16]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 10469071HCID 10469071, compound

Product 1

HCID 211877862-[2-(4-Benzhydrylsulfanyl-piperidin-1-yl)-ethyl]-isoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The mixture of 4-benzhydrylsulfanyl-piperidine (12 mg, 0.0423 mmol, 1.0 eq.), N-(2-bromoethyl)phthalimide (11 mg, 0.0423 mmol, 1.0 eq.), K2CO3 (9 mg, 0.0635 mmol, 1.5 eq.), and NaI (9 mg, 0.0600 mmol, 1.4 eq.) in 2-butanone (5 ml) was refluxed for 2-3 hours. The mixture was then cooled to room temperature. The solvent was removed and the resulted residue was dissolved in CHCl3 (25 ml). The solution was washed with water (3×5 ml), then dried over anhydrous Na2SO4. After removed all solvent, the crude product 2-[2-(4-benzhydrylsulfanyl-piperidin-1-yl)-ethyl]-isoindole-1,3-dione was yielded (15 mg).

Workup

  1. temperaturewas refluxed for 2-3 hours
  2. customThe solvent was removed
  3. dissolutionthe resulted residue was dissolved in CHCl3 (25 ml)
  4. washThe solution was washed with water (3×5 ml)
  5. dry with materialdried over anhydrous Na2SO4
  6. customAfter removed all solvent

Sources & evidence

ORD record
ord-7579b1066a804960ad07d7df83aaa3ca
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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