Sodium Iodide → 2-{2-[4-(1,1-Diphenyl-methoxymethyl)-piperidin-1-yl]-ethyl}-isoindole-1,3-dione

HRID 1383456Notes

Reaction equation

HRID 1383456 reaction equation
[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=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>[C:1]1([CH:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([CH2:23][CH2:24][N:25]3[C:26](=[O:35])[C:27]4[C:28](=[CH:31][CH:32]=[CH:33][CH:34]=4)[C:29]3=[O:30])[CH2:12][CH2:11]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 27624204-((Diphenylmethoxy)methyl)piperidine

Product 1

HCID 543500052-{2-[4-(1,1-Diphenyl-methoxymethyl)-piperidin-1-yl]-ethyl}-isoindole-1,3-dioneYield 79.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The mixture of 4-(1,1-diphenyl-methoxymethyl)-piperidine (0.760 g, 2.7 mmol, 1.0 eq.), N-(2-bromoethyl)phthalimide (0.686 g, 2.7 mmol, 1.0 eq.), K2CO3 (0.560 g, 4.1 mmol, 1.5 eq.), and NaI (0.567 g, 3.8 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 (80 ml). The solution was washed with water (3×10 ml), then dried over anhydrous Na2SO4. After removed all solvent, the crude product 2-{2-[4-(1,1-diphenyl-methoxymethyl)-piperidin-1-yl]-ethyl}-isoindole-1,3-dione was yielded (0.980 g, 79.8% 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 (80 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-b721ecc1f23c49c2a3800d289e189de9
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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