Potassium Iodide → 1-[4-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-butyl]-4,4-dimethyl-piperidine-2,6-dione

HRID 1262548Notes

Reaction equation

HRID 1262548 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:11](=[O:12])[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7]1=[O:15].[N:16]1([C:22]2[C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[S:24][N:23]=2)[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[S:24]1[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:22]([N:16]2[CH2:17][CH2:18][N:19]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:11](=[O:12])[CH2:10][C:9]([CH3:14])([CH3:13])[CH2:8][C:7]3=[O:15])[CH2:20][CH2:21]2)=[N:23]1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27721443-(1-Piperazinyl)-1,2-benzisothiazoleHCID 136603351-(4-Bromobutyl)-4,4-dimethylpiperidine-2,6-dione

Product 1

HCID 132324931-[4-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-butyl]-4,4-dimethyl-piperidine-2,6-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(4-bromobutyl)-3,3-dimethylglutarimide (4 g., 0.0145 mole) obtained according to the procedure of Example 9, 3-(1-piperazinyl)-1,2-benzisothiazole (3.18 g., 0.0145 mole), anhydrous potassium carbonate (20.04 g., 0.145 mole) and potassium iodide (0.25 g., 0.0015 mole) in 150 ml. of acetonitrile is stirred and refluxed for a period of 12 hr. The reaction mixture is filtered, concentrated in vacuo and residual material triturated with ether. Crystallization of the solid thus obtained from ether affords a 64% yield of analytically pure 1-[4-[4-(1,2-benzisothiazol-3-yl)-1-piperazinyl]butyl]-4,4-dimethyl-2,6-piperidinedione, m.p. 146°-147° C.

Workup

  1. customobtained
  2. temperaturerefluxed for a period of 12 hr
  3. filtrationThe reaction mixture is filtered
  4. concentrationconcentrated in vacuo and residual material
  5. customtriturated with ether
  6. customCrystallization of the solid
  7. customthus obtained from ether

Sources & evidence

ORD record
ord-4ee7ab1d3b7b470290fa374199e17d71
Source dataset
uspto-grants-1984_06
Patent number
US04452799

Reaction notes

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