Sodium Iodide → 3-(4-(1-(6-Chlorobenzo[b]thiophen-3-yl)-4-piperazinyl)butyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one hydrochloride

HRID 484155Notes

Reaction equation

HRID 484155 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].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[C:25]([N:26]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]3)=[CH:24][S:23][C:22]=2[CH:32]=1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>C(#N)C>[ClH:17].[Cl:17][C:18]1[CH:19]=[CH:20][C:21]2[C:25]([N:26]3[CH2:27][CH2:28][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][N:6]4[C:10](=[O:11])[C:9]5([CH2:15][CH2:14][CH2:13][CH2:12]5)[S:8][CH:7]4[CH3:16])[CH2:30][CH2:31]3)=[CH:24][S:23][C:22]=2[CH:32]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 107809503-(4-Bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-oneHCID 155414601-(6-Chlorobenzo[b]thien-3-yl)-piperazine

Product 1

HCID 148561783-(4-(1-(6-Chlorobenzo[b]thiophen-3-yl)-4-piperazinyl)butyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one hydrochlorideYield 27.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-(4-bromobutyl)-2-methyl-1-thia-3-azaspiro[4.4]nonan-4-one (5.00 g), 6-chloro-3-piperazinylbenzo[b]thiophene (5.10 g), K2CO3 (8.00 g) and NaI (400 mg) in acetonitrile (250 ml) was heated at 85° C. for 15.5 hours and the product was processed in substantially the same manner as in Example 10 to afford 1.43 g of crystalline solid, m.p. 211°-214° C.

Sources & evidence

ORD record
ord-4eabe4d8eb094d10af6285edf7e57c54
Source dataset
uspto-grants-1993_07
Patent number
US05229388

Reaction notes

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