4-Nitrobenzenesulfonyl chloride → (4-Fluorophenyl)-[4-(4-nitrophenyl)sulfonylpiperazin-1-yl]methanone

HRID 568897Notes

Reaction equation

HRID 568897 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10](Cl)(=[O:12])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[F:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1.[H][H]>C(O)C>[F:15][C:16]1[CH:29]=[CH:28][C:19]([C:20]([N:22]2[CH2:27][CH2:26][N:25]([S:10]([C:7]3[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH2:24][CH2:23]2)=[O:21])=[CH:18][CH:17]=1.[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:25]2[CH2:24][CH2:23][N:22]([C:20](=[O:21])[C:19]3[CH:18]=[CH:17][C:16]([F:15])=[CH:29][CH:28]=3)[CH2:27][CH2:26]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 74044-Nitrobenzenesulfonyl chlorideHCID 20149590(4-Fluorophenyl)(piperazin-1-yl)methanone hydrochlorideHCID 178418361HCID 178418361, compound

Product 2

HCID 1151463(4-Fluorophenyl)-[4-(4-nitrophenyl)sulfonylpiperazin-1-yl]methanoneHCID 201903941-(4-Aminobenzenesulphonyl)-4-(4-fluorobenzoyl)piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-fluorobenzoyl)-4-(4-nitrobenzenesulphonyl) piperazine is prepared in a similar manner to Examples 1 and 2 by reacting equimolar quantities of 4-nitrobenzenesulphonyl chloride with 1-(4-fluorobenzoyl)piperazine hydrochloride. The reaction product is hydrogenated in ethanol at room temperature at atmospheric pressure with a 5% paladium on charcoal catalyst until hydrogen uptake ceases to yield 1-(4-aminobenzenesulphonyl)-4-(4-fluorobenzoyl) piperazine. Equimolar quantities of this compound and 4-chloro-7-trifluoroquinoline are reacted in 50% aqueous ethanol under reflux to yield the title compound.

Sources & evidence

ORD record
ord-0b92fedd0018472caa7fbe70cb951457
Source dataset
uspto-grants-1988_03
Patent number
US04730047

Reaction notes

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