Sodium Iodide → 3-(4-(1-[1,2-Benzisothiazol-3-yl]-4-piperazinyl)-butyl)-2,5,5-trimethyl-4-thiazolidinone hydrochloride

HRID 484151Notes

Reaction equation

HRID 484151 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][N:6]1[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH:7]1[CH3:14].[ClH:15].[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)=[N:17]1.S1C2C=CC=CC=2C(N2CCNCC2)=N1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[ClH:15].[S:16]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18]([N:25]2[CH2:26][CH2:27][N:28]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]3[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH:7]3[CH3:14])[CH2:29][CH2:30]2)=[N:17]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107790943-(4-Bromobutyl)-2,5,5-trimethyl-4-thiazolidinoneHCID 217066301-(1,2-Benzisothiazol-3-yl)piperazine 1-(1,2-benzisothiazol-3-yl)piperazine hydrochloride

Product 1

HCID 148561503-(4-(1-[1,2-Benzisothiazol-3-yl]-4-piperazinyl)-butyl)-2,5,5-trimethyl-4-thiazolidinone hydrochlorideYield 61.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 3-(4-bromobutyl)-2,5,5-trimethyl-4-thiazolidinone (4.70 g), 1-(1,2-benzisothiazol-3-yl)piperazine 1-(1,2-benzisothiazol-3-yl)piperazine hydrochloride (4.72 g), K2CO3 (8.13 g) and NaI (300 mg) in acetonitrile (200 ml) was heated at 65° C. for 16 hours and the product was processed in substantially the same manner as in Example 10 to afford 2.77 g of crystals, m.p. 209°-214° C.

Sources & evidence

ORD record
ord-5caa3f08ee3848bc8c832ea4442baeb4
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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