(4-fluorophenyl)-piperazin-1-ylmethanone;hydrochloride

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (7.8 g, 0.02 mol) was added portion-wise with stirring to a cold mixture of 1-(4-fluorobenzoyl) piperazine hydrochloride (4.9 g, 0.02 mol) in chloroform (250 ml) and sodium carbonate (24.4 g) in water (250 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After 1 hour the chloroform layer was separated and dried (MgSO4). The solvent was removed by evaporation to give a brown gum. Crystallisation from ethanol gave the pure title compound (0.53 g), m.p. 235°-237° C. The cooling bath was removed After 1 hour the chloroform layer was separated dried (MgSO4) The solvent was removed by evaporation to give a brown gum Crystallisation from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (3.5 g, 0.008 mol) was added portionwise to a cold (10°), well stirred mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (2.0 g, 0.008 mol) in chloroform (50 ml) and sodium carbonate (10.0 g) in water (50 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After half an hour, the mixture was filtered and the filtrate separated. The chloroform layer was dried (MgSO4). The solvent was removed by evaporation to give a yellow gum. The gum was crystallised from ethanol-water, then purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol, to give the pure title compound (0.9 g), m.p. 172°-174.5° C. The cooling bath was removed After half an hour the mixture was filtered the filtrate separated The chloroform layer was dried (MgSO4) The solvent was removed by evaporation to give a yellow gum The gum was crystallised from ethanol-water purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (3.5 g, 0.008 mol) was added portionwise to a cold (10°), well stirred mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (2.0 g, 0.008 mol) in chloroform (50 ml) and sodium carbonate (10.0 g) in water (50 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After half an hour, the mixture was filtered and the filtrate separated. The chloroform layer was dried (MgSO4). The solvent was removed by evaporation to give a yellow gum. The gum was crystallised from ethanol-water, then purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol, to give the pure title compound (0.9 g), m.p. 172°-174.5° C. The cooling bath was removed After half an hour the mixture was filtered the filtrate separated The chloroform layer was dried (MgSO4) The solvent was removed by evaporation to give a yellow gum The gum was crystallised from ethanol-water purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (7.8 g, 0.02 mol) was added portionwise with stirring to a cold mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (4.9 g, 0.02 mol) in chloroform (250 ml) and sodium carbonate (24.4 g) in water (250 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After 1 hour the chloroform layer was separated and dried (MgSO4). The solvent was removed by evaporation to give a brown gum. Crystallisation from ethanol gave the pure title compound (0.53 g), m.p. 235°-237° C. The cooling bath was removed After 1 hour the chloroform layer was separated dried (MgSO4) The solvent was removed by evaporation to give a brown gum Crystallisation from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (3.5 g, 0.008 mol) was added portionwise to a cold (10°), well stirred mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (2.0 g, 0.008 mol) in chloroform (50 ml) and sodium carbonate (10.0 g) in water (50 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After half an hour, the mixture was filtered and the filtrate separated. The chloroform layer was dried (MgSO4). The solvent was removed by evaporation to give a yellow gum. The gum was crystallised from ethanol-water, then purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol, to give the pure title compound (0.9 g), m.p. 172°-174.5° C. The cooling bath was removed After half an hour the mixture was filtered the filtrate separated The chloroform layer was dried (MgSO4) The solvent was removed by evaporation to give a yellow gum The gum was crystallised from ethanol-water purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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.

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-(7-Chloro-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (7.8 g, 0.02 mol) was added portion-wise with stirring to a cold mixture of 1-(4-fluorobenzoyl) piperazine hydrochloride (4.9 g, 0.02 mol) in chloroform (250 ml) and sodium carbonate (24.4 g) in water (250 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After 1 hour the chloroform layer was separated and dried (MgSO4). The solvent was removed by evaporation to give a brown gum. Crystallisation from ethanol gave the pure title compound (0.53 g), m.p. 235°-237° C. The cooling bath was removed After 1 hour the chloroform layer was separated dried (MgSO4) The solvent was removed by evaporation to give a brown gum Crystallisation from ethanol

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4-(7-Trifluoromethyl-4-quinolinylamino)benzenesulphonyl chloride hydrochloride (3.5 g, 0.008 mol) was added portionwise to a cold (10°), well stirred mixture of 1-(4-fluorobenzoyl)piperazine hydrochloride (2.0 g, 0.008 mol) in chloroform (50 ml) and sodium carbonate (10.0 g) in water (50 ml). The cooling bath was removed and the mixture was allowed to warm to room temperature. After half an hour, the mixture was filtered and the filtrate separated. The chloroform layer was dried (MgSO4). The solvent was removed by evaporation to give a yellow gum. The gum was crystallised from ethanol-water, then purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol, to give the pure title compound (0.9 g), m.p. 172°-174.5° C. The cooling bath was removed After half an hour the mixture was filtered the filtrate separated The chloroform layer was dried (MgSO4) The solvent was removed by evaporation to give a yellow gum The gum was crystallised from ethanol-water purified by column chromatography (basic Al2O3-chloroform) followed by recrystallisation from ethanol