1H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)- → HCID 18467338, compound

HRID 2257683Notes

Reaction equation

HRID 2257683 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]3)=[N:7][S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][CH2:25][N:26]1[C:30](=[O:31])[C:29]2=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36]>C(#N)C>[F:1][C:2]1[CH:16]=[CH:15][C:5]2[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([CH2:24][CH2:25][N:26]4[C:30](=[O:31])[C:29]5=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]5[C:27]4=[O:36])[CH2:13][CH2:14]3)=[N:7][S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 113251H-Isoindole-1,3(2H)-dione, 2-(2-bromoethyl)-HCID 11430Potassium CarbonateHCID 185049766-Fluoro-3-(4-piperidinyl)-1,2-benzisothiazole

Product 1

HCID 18467338HCID 18467338, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred mixture of 6-fluoro-3-(4-piperidinyl)-1,2-benzisothiazole (4.72 g, 0.02 mole), potassium carbonate (4.14 g, 0.03 mole) and N-(2-bromoethyl)phthalimide (6.35 g, 0.025 mole) in 200 ml of acetonitrile is heated at reflux for 4 hours. The solids are then removed by filtration and the filtrate is concentrated under reduced pressure. The residue is purified by chromatography over silica gel to provide N-[2-[4-(6-fluoro-1,2-benzisothiazol-3-yl)-1-piperidinyl]ethyl]phthalimide.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 4 hours
  3. customThe solids are then removed by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by chromatography over silica gel

Sources & evidence

ORD record
ord-c7f71d22f6784a4b8724a7df65d32843
Source dataset
uspto-grants-1997_08
Patent number
US05658911

Reaction notes

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