Potassium Iodide → 8-[4-[4-(2,1-Benzisothiazol-3-yl)-1-piperazinyl]butyl]-8-azaspiro[4.5]decane-7,9-dione
Reaction equation
O.O.Cl.Cl.[N:5]1([C:11]2[S:12][N:13]=[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=23)[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1.Br[CH2:21][CH2:22][CH2:23][CH2:24][N:25]1[C:34](=[O:35])[CH2:33][C:28]2([CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:27][C:26]1=[O:36].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[N:13]1[S:12][C:11]([N:5]2[CH2:10][CH2:9][N:8]([CH2:21][CH2:22][CH2:23][CH2:24][N:25]3[C:26](=[O:36])[CH2:27][C:28]4([CH2:32][CH2:31][CH2:30][CH2:29]4)[CH2:33][C:34]3=[O:35])[CH2:7][CH2:6]2)=[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=12Participants
Reactant 5
Product 1
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.).
Sources & evidence
- ORD record
- ord-e20dd3ab297544748f8b5f1f4c2751d0
- Source dataset
- uspto-grants-1984_06
- Patent number
- US04452799
Reaction notes
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