Sodium Iodide → 3-(4-(1-[1,2-Benzisothiazol-3-yl]-4-piperazinyl)butyl)1-thia-3-azaspiro[4.5]decan-4-one

HRID 846445Notes

Reaction equation

HRID 846445 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[S:8][CH2:7]1.Cl.[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[N:18]1.[C:32]([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[S:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19]([N:26]2[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[C:9]4([CH2:15][CH2:14][CH2:13][CH2:12][CH2:32]4)[S:8][CH2:7]3)[CH2:30][CH2:31]2)=[N:18]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107087473-(4-Bromobutyl)-1-thia-3-azaspiro[4.4]nonan-4-oneHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride

Product 1

HCID 106469683-(4-(1-[1,2-Benzisothiazol-3-yl]-4-piperazinyl)butyl)1-thia-3-azaspiro[4.5]decan-4-oneYield 49.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-(4-bromobutyl)-1-thia-3-azaspiro[4.4]nonan-4-one (4.00 g), 1-(1,2-benzisothiazol-3-yl)piperazine hydrochloride (3.67 g), K2CO3 (7.00 g) and NaI (300 mg) in acetonitrile (220 ml) was heated at 70° C. for 20 hours and the product was processed in substantially the same manner as in Example 10 to afford 3.01 g of crystalline solid, m.p. 209° C.

Sources & evidence

ORD record
ord-79f9369865c34b3fa567fa6e7470d9c4
Source dataset
uspto-grants-1992_08
Patent number
US05136037

Reaction notes

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