Potassium Iodide → 8-[4-[4-(2,1-Benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione

HRID 648204Notes

Reaction equation

HRID 648204 reaction equation
[N:1]1([C:7]2[S:8][N:9]=[C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=23)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:17][CH2:18][CH2:19][CH2:20][N:21]1[C:30](=[O:31])[CH2:29][C:24]2([CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:23][C:22]1=[O:32].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[N:9]1[S:8][C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:17][CH2:18][CH2:19][CH2:20][N:21]3[C:22](=[O:32])[CH2:23][C:24]4([CH2:28][CH2:27][CH2:26][CH2:25]4)[CH2:29][C:30]3=[O:31])[CH2:3][CH2:2]2)=[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=12

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 112088518-(4-Bromobutyl)-8-azaspiro(4.5)decane-7,9-dioneHCID 132325103-(1-Piperazinyl)-2,1-benzisothiazole

Product 1

HCID 132324978-[4-[4-(2,1-Benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dioneYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Title product dihydrochloride dihydrate. A mixture of 3-(1-piperazinyl)-2,1-benzisothiazole (4.0 g., 0.018 mole) and 8-(4-bromobutyl)-8-azaspiro[4.5]decane-7,9-dione (5.5 g., 0.018 mole), anhydrous potassium carbonate (4.98 g., 0.036 mole) and potassium iodide (0.83 g., 0.005 mole) in 100 ml. of acetonitrile is stirred at reflux temperature for a period of 20 hr. The reaction mixture is filtered, concentrated in vacuo and residual material triturated with ether to afford 7.38 g., (93% yield) of the title product free base. Conversion of the free base to the hydrochloride salt in ethanol with ethanolic hydrogen chloride and crystallization from ethanol affords 5.34 g. (57% yield) of analytically pure 8-[4-[4-(2,1-benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspiro-[4.5]decane-7,9-dione dihydrochloride hemihydrate, m.p. 225°-227° C. (dec.).

Workup

  1. temperatureat reflux temperature for a period of 20 hr
  2. filtrationThe reaction mixture is filtered
  3. concentrationconcentrated in vacuo and residual material
  4. customtriturated with ether
  5. customto afford 7.38 g

Sources & evidence

ORD record
ord-be9da5238836476e8b8e6f6c1c4b20c7
Source dataset
uspto-grants-1983_10
Patent number
US04411901

Reaction notes

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