2-ethylpiperazine;hydrochloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a methylene chloride solution (30 ml) of 2-ethylpiperazine hydrochloride (307 mg) was added (6-chlorobenzo[b]thien-2-yl)sulfonyl chloride (438 mg) and triethylamine (498 mg). The resulting mixture was stirred at room temperature for 26 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:20), whereby the title compound (255 mg) was obtained as a pale yellow oil. MS (FAB) m/z: 345 [(M+H)+, Cl35], 347 [(M+H)+, Cl37]. 1H-NMR (CDCl3) δ: 0.95(3H,t,J=7.8 Hz), 1.24-1.46(2H,m), 2.16(1H,t,J=10.7 Hz), 2.54(1H,dt,J=2.9,11.2 Hz), 2.65-2.75(1H,m), 2.95(1H,dt,J=2.9,11.2 Hz), 3.04-3.10(1H,m), 3.65-3.72(2H,m), 7.43(1H,dd,J=8.8,2.0 Hz), 7.75(1H,s), 7.81(1H,d,J=8.8 Hz), 7.86(1H,s). the water layer was extracted three times dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent was obtained as a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a methylene chloride solution (700 ml) of 2-ethylpiperazine hydrochloride (5.00 g) were added 5-chloro -1-phenylsulfonylindol-2-sulfonyl chloride (7.14 g) and triethylamine (11.16 ml) and the resulting mixture was stirred at room temperature for 3 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g) was obtained as a pale yellow oil. the water layer was extracted three times dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g) was obtained as a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, concentrated hydrochloric acid (6 ml) and palladium hydroxide (1.1 g) were added to solution (600 ml) of 1,4-dibenzyl-2-ethenylpiperazine (10.9 g)in ethanol, followed by stirring for 12 hours under a hydrogen gas stream of 1 atmospheric pressure. The catalyst was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was solidified using methylene chloride—diethyl ether, followed by washing with diethyl ether. The resulting solid was dried under reduced pressure, whereby the title compound (6.516 g) was obtained as a brown solid. The catalyst was filtered off the solvent was distilled off under reduced pressure by washing with diethyl ether The resulting solid was dried under reduced pressure, whereby the title compound (6.516 g) was obtained as a brown solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a methylene chloride solution (30 ml) of 2-ethylpiperazine hydrochloride (307 mg) was added (6-chlorobenzo[b]thien-2-yl)sulfonyl chloride (438 mg) and triethylamine (498 mg). The resulting mixture was stirred at room temperature for 26 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:20), whereby the title compound (255 mg) was obtained as a pale yellow oil. MS (FAB) m/z: 345 [(M+H)+, Cl35], 347 [(M+H)+, Cl37]. 1H-NMR (CDCl3) δ: 0.95(3H,t,J=7.8 Hz), 1.24-1.46(2H,m), 2.16(1H,t,J=10.7 Hz), 2.54(1H,dt,J=2.9,11.2 Hz), 2.65-2.75(1H,m), 2.95(1H,dt,J=2.9,11.2 Hz), 3.04-3.10(1H,m), 3.65-3.72(2H,m), 7.43(1H,dd,J=8.8,2.0 Hz), 7.75(1H,s), 7.81(1H,d,J=8.8 Hz), 7.86(1H,s). the water layer was extracted three times dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent was obtained as a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a methylene chloride solution (30 ml) of 2-ethylpiperazine hydrochloride (307 mg) was added (6-chlorobenzo[b]thien-2-yl)sulfonyl chloride (438 mg) and triethylamine (498 mg). The resulting mixture was stirred at room temperature for 26 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:20), whereby the title compound (255 mg) was obtained as a pale yellow oil. MS (FAB) m/z: 345 [(M+H)+, Cl35], 347 [(M+H)+, Cl37]. 1H-NMR (CDCl3) δ: 0.95(3H,t,J=7.8 Hz), 1.24-1.46(2H,m), 2.16(1H,t,J=10.7 Hz), 2.54(1H,dt,J=2.9,11.2 Hz), 2.65-2.75(1H,m), 2.95(1H,dt,J=2.9,11.2 Hz), 3.04-3.10(1H,m), 3.65-3.72(2H,m), 7.43(1H,dd,J=8.8,2.0 Hz), 7.75(1H,s), 7.81(1H,d,J=8.8 Hz), 7.86(1H,s). the water layer was extracted three times dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent was obtained as a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a methylene chloride solution (700 ml) of 2-ethylpiperazine hydrochloride (5.00 g) were added 5-chloro -1-phenylsulfonylindol-2-sulfonyl chloride (7.14 g) and triethylamine (11.16 ml) and the resulting mixture was stirred at room temperature for 3 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g) was obtained as a pale yellow oil. the water layer was extracted three times dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g) was obtained as a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, concentrated hydrochloric acid (6 ml) and palladium hydroxide (1.1 g) were added to solution (600 ml) of 1,4-dibenzyl-2-ethenylpiperazine (10.9 g)in ethanol, followed by stirring for 12 hours under a hydrogen gas stream of 1 atmospheric pressure. The catalyst was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was solidified using methylene chloride—diethyl ether, followed by washing with diethyl ether. The resulting solid was dried under reduced pressure, whereby the title compound (6.516 g) was obtained as a brown solid. The catalyst was filtered off the solvent was distilled off under reduced pressure by washing with diethyl ether The resulting solid was dried under reduced pressure, whereby the title compound (6.516 g) was obtained as a brown solid

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a methylene chloride solution (30 ml) of 2-ethylpiperazine hydrochloride (307 mg) was added (6-chlorobenzo[b]thien-2-yl)sulfonyl chloride (438 mg) and triethylamine (498 mg). The resulting mixture was stirred at room temperature for 26 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was subjected to chromatography on a silica gel column (methanol:methylene chloride=1:20), whereby the title compound (255 mg) was obtained as a pale yellow oil. MS (FAB) m/z: 345 [(M+H)+, Cl35], 347 [(M+H)+, Cl37]. 1H-NMR (CDCl3) δ: 0.95(3H,t,J=7.8 Hz), 1.24-1.46(2H,m), 2.16(1H,t,J=10.7 Hz), 2.54(1H,dt,J=2.9,11.2 Hz), 2.65-2.75(1H,m), 2.95(1H,dt,J=2.9,11.2 Hz), 3.04-3.10(1H,m), 3.65-3.72(2H,m), 7.43(1H,dd,J=8.8,2.0 Hz), 7.75(1H,s), 7.81(1H,d,J=8.8 Hz), 7.86(1H,s). the water layer was extracted three times dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent was obtained as a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a methylene chloride solution (700 ml) of 2-ethylpiperazine hydrochloride (5.00 g) were added 5-chloro -1-phenylsulfonylindol-2-sulfonyl chloride (7.14 g) and triethylamine (11.16 ml) and the resulting mixture was stirred at room temperature for 3 hours. Distilled water and methylene chloride were added and the water layer was extracted three times. The organic layers were combined, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g) was obtained as a pale yellow oil. the water layer was extracted three times dried over anhydrous sodium sulfate distilled under reduced pressure to remove the solvent The residue was purified by chromatography on a silica gel column (methanol:methylene chloride=1:100), whereby the title compound (5.86 g) was obtained as a pale yellow oil

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: At room temperature, concentrated hydrochloric acid (6 ml) and palladium hydroxide (1.1 g) were added to solution (600 ml) of 1,4-dibenzyl-2-ethenylpiperazine (10.9 g)in ethanol, followed by stirring for 12 hours under a hydrogen gas stream of 1 atmospheric pressure. The catalyst was filtered off and the solvent was distilled off under reduced pressure. The resulting residue was solidified using methylene chloride—diethyl ether, followed by washing with diethyl ether. The resulting solid was dried under reduced pressure, whereby the title compound (6.516 g) was obtained as a brown solid. The catalyst was filtered off the solvent was distilled off under reduced pressure by washing with diethyl ether The resulting solid was dried under reduced pressure, whereby the title compound (6.516 g) was obtained as a brown solid