Sodium Iodide → HCID 13912336, compound

HRID 1383453Notes

Reaction equation

HRID 1383453 reaction equation
[CH:1]([O: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]([O: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 30175844-Benzhydryloxypiperidine

Product 1

HCID 13912336HCID 13912336, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The mixture of 4-benzhydryloxy-piperidine (1.85 g, 3.4 mmol, 1.0 eq.), N-(2-bromoethyl)phthalimide (0.855 g, 3.4 mmol, 1.0 eq.), K2CO3 (0.705 g, 5.1 mmol, 1.5 eq.), and NaI (0.713 g, 4.8 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 (3×10 ml), then dried over anhydrous Na2SO4. After removed all solvent, the crude product, 2-[2-(4-benzhydryloxy-piperidin-1-yl)-ethyl]-isoindole-1,3-dione was yielded (1.5 g, 100% yield). 1H-NMR (CDCl3, ppm): 7.84 (m, 2H), 7.70 (m, 2H), 7.20-7.40 (m, 10H), 5.50 (s, 1H), 3.80 (t, 2H), 3.39 (m, 1H), 2.82 (m, 2H), 2.59 (t, 2H), 2.18 (m, 2H), 1.83 (m, 2H) 1.67 (m, 2H). ESMS 441.2 (M+1), 463.2 (M+23).

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-b37f6609faae4e13a519f58757d88da9
Source dataset
uspto-grants-2001_07
Patent number
US06255323B1

Reaction notes

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