Sodium Iodide → 3-(4-(1-(6-Chlorobenzo[b]thiophen-3-yl)-4-piperazinyl)butyl)-2,5,5-trimethyl-4-thiazolidinone hydrochloride

HRID 484149Notes

Reaction equation

HRID 484149 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].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[C:23]([N:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)=[CH:22][S:21][C:20]=2[CH:30]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[ClH:15].[Cl:15][C:16]1[CH:17]=[CH:18][C:19]2[C:23]([N:24]3[CH2:25][CH2:26][N:27]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10](=[O:11])[C:9]([CH3:13])([CH3:12])[S:8][CH:7]4[CH3:14])[CH2:28][CH2:29]3)=[CH:22][S:21][C:20]=2[CH:30]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107790943-(4-Bromobutyl)-2,5,5-trimethyl-4-thiazolidinoneHCID 155414601-(6-Chlorobenzo[b]thien-3-yl)-piperazine

Product 1

HCID 217065883-(4-(1-(6-Chlorobenzo[b]thiophen-3-yl)-4-piperazinyl)butyl)-2,5,5-trimethyl-4-thiazolidinone hydrochlorideYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-(4-bromobutyl)-2,5,5-trimethyl-4-thiazolidinone (5.00 g), 6-chloro-3-piperazinylbenzo[b]thiophene (5.41 g), K2CO3 (8.63 g) and NaI (400 mg) in acetonitrile (200 ml) was heated at 90° C. for 16.5 hours and the product was processed in substantially the same manner as in Example 10 to afford 2.25 g of powder, m.p. 199°-202° C.

Sources & evidence

ORD record
ord-a33e3aa000fc4145b3beba2b2264bf55
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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