1-heptylpiperazine

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 2-((1-naphthyloxy)methyl)oxirane (106 mg, 0.53 mmol) in ethanol (1 mL) was added 4-heptylpiperazine (118 mg, 0.64 mmol) at room temperature. The mixture was stirred under reflux for 1 hr. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give HUHS1018 (188 mg, 93%). under reflux for 1 hr The reaction mixture was concentrated under reduced pressure The crude product was purified by silica gel column chromatography

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

Procedure: A mixture of 1.15 g of 2-(3-pyridyl)-1-pyrroline-4-carboxylic acid monohydrobromide, 770 mg of 1-heptylpiperazine, 860 mg of dicyclohexylcarbodiimide and 560 mg of 1-hydroxybenzotriazole in 15 ml of N,N-dimethylformamide was stirred at room temperature for 3 days. After dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off, the filtrate was concentrated under reduced pressure and, after addition of 0.5N aqueous sodium hydroxide, the residue was extracted with ethyl acetate. The organic layer was extracted with 1N hydrochloric acid. The aqueous layer was adjusted to pH 10 by addition of potassium carbonate and extracted again with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (15 g). Elution with ethyl acetate gave 1.01 g of 1-heptyl-4-[2-(3-pyridyl)-2-pyrrolin-5-ylcarbonyl]piperazine. After dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off the filtrate was concentrated under reduced pressure after addition of 0.5N aqueous sodium hydroxide the residue was extracted with ethyl acetate The organic layer was extracted with 1N hydrochloric acid The aqueous layer was adjusted to pH 10 by addition of potassium carbonate extracted again with ethyl acetate The organic layer was washed with saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate concentrated under reduced pressure Elution with ethyl acetate

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

Procedure: A mixture of 1.15 g of 2-(3-pyridyl)-1-pyrroline-4-carboxylic acid monohydrobromide, 770 mg of 1-heptylpiperazine, 860 mg of dicyclohexylcarbodiimide and 560 mg of 1-hydroxybenzotriazole in 15 ml of N,N-dimethylformamide was stirred at room temperature for 3 days. After dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off, the filtrate was concentrated under reduced pressure and, after addition of 0.5N aqueous sodium hydroxide, the residue was extracted with ethyl acetate. The organic layer was extracted with 1N hydrochloric acid. The aqueous layer was adjusted to pH 10 by addition of potassium carbonate and extracted again with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (15 g). Elution with ethyl acetate gave 1.01 g of 1-heptyl-4-[2-(3-pyridyl)-2-pyrrolin-5-ylcarbonyl]piperazine. After dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off the filtrate was concentrated under reduced pressure after addition of 0.5N aqueous sodium hydroxide the residue was extracted with ethyl acetate The organic layer was extracted with 1N hydrochloric acid The aqueous layer was adjusted to pH 10 by addition of potassium carbonate extracted again with ethyl acetate The organic layer was washed with saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate concentrated under reduced pressure Elution with ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: The title compound was prepared from 4-(3-(3-cyanophenyl)ureido)-N-(4-sulfamoylbenzyl)benzenesulfonamide following procedure C and using 1.5 equivalents of n-heptylpiperazine as secondary amine. The product was purified by preparative HPLC. The product was purified by preparative HPLC

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

Procedure: To a solution of 2-((1-naphthyloxy)methyl)oxirane (106 mg, 0.53 mmol) in ethanol (1 mL) was added 4-heptylpiperazine (118 mg, 0.64 mmol) at room temperature. The mixture was stirred under reflux for 1 hr. The reaction mixture was concentrated under reduced pressure. The crude product was purified by silica gel column chromatography to give HUHS1018 (188 mg, 93%). under reflux for 1 hr The reaction mixture was concentrated under reduced pressure The crude product was purified by silica gel column chromatography

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

Procedure: A mixture of 1.15 g of 2-(3-pyridyl)-1-pyrroline-4-carboxylic acid monohydrobromide, 770 mg of 1-heptylpiperazine, 860 mg of dicyclohexylcarbodiimide and 560 mg of 1-hydroxybenzotriazole in 15 ml of N,N-dimethylformamide was stirred at room temperature for 3 days. After dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off, the filtrate was concentrated under reduced pressure and, after addition of 0.5N aqueous sodium hydroxide, the residue was extracted with ethyl acetate. The organic layer was extracted with 1N hydrochloric acid. The aqueous layer was adjusted to pH 10 by addition of potassium carbonate and extracted again with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (15 g). Elution with ethyl acetate gave 1.01 g of 1-heptyl-4-[2-(3-pyridyl)-2-pyrrolin-5-ylcarbonyl]piperazine. After dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off the filtrate was concentrated under reduced pressure after addition of 0.5N aqueous sodium hydroxide the residue was extracted with ethyl acetate The organic layer was extracted with 1N hydrochloric acid The aqueous layer was adjusted to pH 10 by addition of potassium carbonate extracted again with ethyl acetate The organic layer was washed with saturated aqueous solution of sodium chloride dried over anhydrous sodium sulfate concentrated under reduced pressure Elution with ethyl acetate