Sodium Iodide → 3-(4-(1-(1,2-Benzisothiazol-3-yl)-4-piperazinyl)butyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one hydrochloride

HRID 2107488Notes

Reaction equation

HRID 2107488 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][CH:7]1[CH3:16].[ClH:17].[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[N:19]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[ClH:17].[S:18]1[C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([N:27]2[CH2:28][CH2:29][N:30]([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][CH:7]3[CH3:16])[CH2:31][CH2:32]2)=[N:19]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107809503-(4-Bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-oneHCID 115217113-(1-Piperazinyl)-1,2-benzisothiazole monohydrochloride

Product 1

HCID 148561793-(4-(1-(1,2-Benzisothiazol-3-yl)-4-piperazinyl)butyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one hydrochlorideYield 47.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(4-bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one (3.84 g), 1-(1,2-benzisothiazol-3-yl)piperazine hydrochloride (3.49 g), K2CO3 (5.90 g) and NaI (280 mg) in acetonitrile (215 ml) was heated at between 65°-80° C. for 16.5 hours and the product was processed in substantially the same manner as in Example 10 to afford 2.86 g of crystals, m.p. 210°-215° C.

Workup

  1. temperaturewas heated at between 65°-80° C. for 16.5 hours

Sources & evidence

ORD record
ord-c48c443fddc84eaaacde0d997314d5ac
Source dataset
uspto-grants-1990_06
Patent number
US04933453

Reaction notes

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