Sodium Iodide → 3-[4-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-butyl]-1-thia-3-aza-spiro[4.4]nonan-4-one

HRID 846441Notes

Reaction equation

HRID 846441 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([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]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 105027743-[4-(4-Benzo[d]isothiazol-3-yl-piperazin-1-yl)-butyl]-1-thia-3-aza-spiro[4.4]nonan-4-oneYield 33.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-bromobutyl)-1-thia-3-azaspiro[4.4]-nonan-4-one (4.50 g), 1-(1,2-benzisothiazol-3-yl)piperazine hydrochloride (4.33 g), K2CO3 (7.45 g) and NaI (560 mg), in acetonitrile (220 ml) was heated at 65° C. for 14.5 hours and the product was processed in substantially the same manner as in Example 10 to afford 2.25 g of crystals, m.p. 200°-203° C.

Sources & evidence

ORD record
ord-9ef8bf01dd8741d18ec8290e5e7b1069
Source dataset
uspto-grants-1992_08
Patent number
US05136037

Reaction notes

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