2-[4-(2-aminoethyl)piperazin-1-yl]ethanol

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Into a solution of 4-(aminoethyl)piperazine-1-ethanol in chloroform (20 ml) was dropped a solution of 2,6-diisopropylphenyl isocyanate (2.03 g, 10 mmol) in chloroform (20 ml) followed by stirring for 5 minutes. The reaction solution was concentrated in vacuo and the residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvents, chloroform→chloroform:ammonia-saturated methanol =20:1) to provide 2.03 g (yield 54%) of N-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]-N′-(2,6-di-isopropylphenyl)urea. The reaction solution was concentrated in vacuo the residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvents, chloroform→chloroform:ammonia-saturated methanol =20:1)

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

実験手順: Into a solution of 4-(aminoethyl)piperazine-1-ethanol in chloroform (20 ml) was dropped a solution of 2,6-diisopropylphenyl isocyanate (2.03 g, 10 mmol) in chloroform (20 ml) followed by stirring for 5 minutes. The reaction solution was concentrated in vacuo and the residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvents, chloroform→chloroform:ammonia-saturated methanol =20:1) to provide 2.03 g (yield 54%) of N-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]-N′-(2,6-di-isopropylphenyl)urea. The reaction solution was concentrated in vacuo the residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvents, chloroform→chloroform:ammonia-saturated methanol =20:1)

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

実験手順: A solution of 4-(cyanomethyl)piperazine-1-ethanol (1.69 g, 10 mmol) in THF (20 ml) was added to a solution of lithium aluminum hydride in THF (20 ml, 20 mmol) in an argon stream with ice cooling, the mixture was stirred at room temperature for 5 minutes and heated to reflux for 90 minutes. The reaction solution was allowed to cool, diluted with ethanol with ice cooling and stirred at room temperature for 15 minutes after adding an aqueous 1N sodium hydroxide solution thereto. This was filtered off through celite and the filtrate was concentrated in vacuo to provide 4-(aminoethyl)piperazine-1-ethanol. heated to reflux for 90 minutes to cool stirred at room temperature for 15 minutes This was filtered off through celite the filtrate was concentrated in vacuo

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

実験手順: 2-{2-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-ethyl}-isoindole-1,3-dione (370 mg, 1.2 mmol) is dissolved in EtOH (8 mL) and hydrazine hydrate (88 mL, 1.8 mmol) is added at RT. The reaction mixture is then refluxed for 3 h and allowed to cool to RT again. The precipitated product is isolated by filtration, washed subsequently with cold EtOH and dried in HV to give the title compound as a white powder. ES-MS: M+H=174.2. 1HNMR (MeOH-d4) δ 4.24 (bs, 2H), 3.41 (t, 2H), 2.62 (t, 2H), 2.54-2.50 (m, 2H), 2-39-2.201 (m, 10H). The reaction mixture is then refluxed for 3 h The precipitated product is isolated by filtration washed subsequently with cold EtOH dried in HV

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

実験手順: 2-{2-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-ethyl}-isoindole-1,3-dione (370 mg, 1.2 mmol) is dissolved in EtOH (8 mL) and hydrazine hydrate (88 mL, 1.8 mmol) is added at RT. The reaction mixture is then refluxed for 3 h and allowed to cool to RT again. The precipitated product is isolated by filtration, washed subsequently with cold EtOH and dried in HV to give the title compound as a white powder. ES-MS: M+H=174.2. 1HNMR (MeOH-d4) δ 4.24 (bs, 2H), 3.41 (t, 2H), 2.62 (t, 2H), 2.54-2.50 (m, 2H), 2-39-2.201 (m, 10H). The reaction mixture is then refluxed for 3 h The precipitated product is isolated by filtration washed subsequently with cold EtOH dried in HV

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

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

実験手順: Into a solution of 4-(aminoethyl)piperazine-1-ethanol in chloroform (20 ml) was dropped a solution of 2,6-diisopropylphenyl isocyanate (2.03 g, 10 mmol) in chloroform (20 ml) followed by stirring for 5 minutes. The reaction solution was concentrated in vacuo and the residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvents, chloroform→chloroform:ammonia-saturated methanol =20:1) to provide 2.03 g (yield 54%) of N-[2-[4-(2-hydroxyethyl)piperazin-1-yl]ethyl]-N′-(2,6-di-isopropylphenyl)urea. The reaction solution was concentrated in vacuo the residue was purified by a silica gel column chromatography (100 g of silica gel; developing solvents, chloroform→chloroform:ammonia-saturated methanol =20:1)

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

実験手順: A solution of 4-(cyanomethyl)piperazine-1-ethanol (1.69 g, 10 mmol) in THF (20 ml) was added to a solution of lithium aluminum hydride in THF (20 ml, 20 mmol) in an argon stream with ice cooling, the mixture was stirred at room temperature for 5 minutes and heated to reflux for 90 minutes. The reaction solution was allowed to cool, diluted with ethanol with ice cooling and stirred at room temperature for 15 minutes after adding an aqueous 1N sodium hydroxide solution thereto. This was filtered off through celite and the filtrate was concentrated in vacuo to provide 4-(aminoethyl)piperazine-1-ethanol. heated to reflux for 90 minutes to cool stirred at room temperature for 15 minutes This was filtered off through celite the filtrate was concentrated in vacuo

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

実験手順: 2-{2-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-ethyl}-isoindole-1,3-dione (370 mg, 1.2 mmol) is dissolved in EtOH (8 mL) and hydrazine hydrate (88 mL, 1.8 mmol) is added at RT. The reaction mixture is then refluxed for 3 h and allowed to cool to RT again. The precipitated product is isolated by filtration, washed subsequently with cold EtOH and dried in HV to give the title compound as a white powder. ES-MS: M+H=174.2. 1HNMR (MeOH-d4) δ 4.24 (bs, 2H), 3.41 (t, 2H), 2.62 (t, 2H), 2.54-2.50 (m, 2H), 2-39-2.201 (m, 10H). The reaction mixture is then refluxed for 3 h The precipitated product is isolated by filtration washed subsequently with cold EtOH dried in HV