2-ethylpiperazine

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: Benzyl bromide (38.7 g, 0.22 mol) was added in portions to an ice cold (0° C.) solution of 2-ethylpiperazine (25 g, 0.22 mol) in DMF (150 mL) with such a rate that the temperature did not exceed 20° C. The mixture was stirred for 1 h, the solvent was evaporated and the residue was partitioned between CHCl3/0.5 M HCl. The aqueous phase was made alkaline (11M NaOH) and extracted three times with CHCl3. The combined organic phases were dried (MgSO4) and concentrated. The resulting oil was purified by column chromatography on silica using CHCl3, followed by CHCl3/MeOH/NH4OH (95:5:0.3) as eluents to give 31.6 g (70%) of the title compound as a yellowish oil. Anal. (C13H20N2) H, N; C: calc, 76.42 found 75.85; H, N. did not exceed 20° C the solvent was evaporated the residue was partitioned between CHCl3/0.5 M HCl extracted three times with CHCl3 The combined organic phases were dried (MgSO4) concentrated The resulting oil was purified by column chromatography on silica

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

実験手順: Benzyl bromide (38.7 g, 0.22 mol) was added in portions to an ice cold (˜0° C.) solution of 2-ethylpiperazine (25 g, 0.22 mol) in DMF (150 mL) with such a rate that the temperature did not exceed 20° C. The mixture was stirred for 1 h, the solvent was evaporated and the residue was partitioned between CHCl3/0.5 M HCl. The aqueous phase was made alkaline (11M NaOH) and extracted three times with CHCl3. The combined organic phases were dried (MgSO4) and concentrated. The resulting oil was purified by column chromatography on silica using CHCl3, followed by CHCl3/MeOH/NH4OH (95:5:0.3) as eluents to give 31.6 g (70%) of the title compound as a yellowish oil. Anal. (C13H20N2) H, N; C: calc, 76.42 found 75.85; H, N. did not exceed 20° C the solvent was evaporated the residue was partitioned between CHCl3/0.5 M HCl extracted three times with CHCl3 The combined organic phases were dried (MgSO4) concentrated The resulting oil was purified by column chromatography on silica

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.8 g (0.01 mol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (II) and 3.4 g (0.03 mol) of 2-ethylpiperazine in 15 ml of dimethyl sulphoxide is heated at 140° C. for 2 hours. The solution is evaporated under high vacuum, the residue is heated with 30 ml of water to 90° C., the precipitate which has separated out is filtered off with suction, washed with water and methanol and isolated. 1.1 g (31% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-ethyl-1-piperazinyl)quinoline-3-carboxylic acid monohydrate, with a decomposition point of 255°-258° C., is obtained. The solution is evaporated under high vacuum the residue is heated with 30 ml of water to 90° C. the precipitate which has separated out is filtered off with suction washed with water and methanol isolated

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.8 g (0.01 mol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (II) and 3.4 g (0.03 mol) of 2-ethylpiperazine in 15 ml of dimethyl sulphoxide is heated at 140° C. for 2 hours. The solution is evaporated under high vacuum, the residue is heated with 30 ml of water to 90° C., the precipitate which has separated out is filtered off with suction, washed with water and methanol and isolated. 1.1 g (31% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-ethyl-1-piperazinyl)quinoline-3-carboxylic acid monohydrate, with a decomposition point of 255°-258° C., is obtained. The solution is evaporated under high vacuum the residue is heated with 30 ml of water to 90° C. the precipitate which has separated out is filtered off with suction washed with water and methanol isolated

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: Benzyl bromide (38.7 g, 0.22 mol) was added in portions to an ice cold (˜0° C.) solution of 2-ethylpiperazine (25 g, 0.22 mol) in DMF (150 mL) with such a rate that the temperature did not exceed 20° C. The mixture was stirred for 1 h, the solvent was evaporated and the residue was partitioned between CHCl3/0.5 M HCl. The aqueous phase was made alkaline (11M NaOH) and extracted three times with CHCl3. The combined organic phases were dried (MgSO4) and concentrated. The resulting oil was purified by column chromatography on silica using CHCl3, followed by CHCl3/MeOH/NH4OH (95:5:0.3) as eluents to give 31.6 g (70%) of the title compound as a yellowish oil. Anal. (C13H20N2) H, N; C: calc, 76.42 found 75.85; H, N. did not exceed 20° C the solvent was evaporated the residue was partitioned between CHCl3/0.5 M HCl extracted three times with CHCl3 The combined organic phases were dried (MgSO4) concentrated The resulting oil was purified by column chromatography on silica

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

実験手順: Benzyl bromide (38.7 g, 0.22 mol) was added in portions to a chilled (˜0° C.) solution of 2-ethylpiperazine (25 g, 0.22 mol) in DMF (150 mL) with such a rate that the temperature did not exceed 20° C. The mixture was stirred for 1 h, the solvent was evaporated and the residue was partitioned between CHCl3/0.5 M aqueous HCl. The aqueous phase was made alkaline (11 M NaOH) and extracted three times with CHCl3. The combined organic phases were dried (MgSO4) and concentrated. The resulting oil was purified by column chromatography on silica using CHCl3, followed by CHCl3/MeOH/NH4OH (95:5:0.3) as eluents to give 31.6 g (70%) of the title compound as a yellowish oil. Anal. (C13H20N2) H, N; C: calcd, 76.42; found, 75.85. did not exceed 20° C the solvent was evaporated the residue was partitioned between CHCl3/0.5 M aqueous HCl extracted three times with CHCl3 The combined organic phases were dried (MgSO4) concentrated The resulting oil was purified by column chromatography on silica

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

実験手順: Benzyl bromide (38.7 g, 0.22 mol) was added in portions to a chilled (˜0° C.) solution of 2-ethylpiperazine (25 g, 0.22 mol) in DMF (150 mL) with such a rate that the temperature did not exceed 20° C. The mixture was stirred for 1 h, the solvent was evaporated and the residue was partitioned between CHCl3/0.5 M aqueous HCl. The aqueous phase was made alkaline (11 M NaOH) and extracted three times with CHCl3. The combined organic phases were dried (MgSO4) and concentrated. The resulting oil was purified by column chromatography on silica using CHCl3, followed by CHCl3/MeOH/NH4OH (95:5:0.3) as eluents to give 31.6 g (70%) of the title compound as a yellowish oil. Anal. (C13H20N2) H, N; C: calcd, 76.42; found, 75.85. *Described in WO 00/76984. did not exceed 20° C the solvent was evaporated the residue was partitioned between CHCl3/0.5 M aqueous HCl extracted three times with CHCl3 The combined organic phases were dried (MgSO4) concentrated The resulting oil was purified by column chromatography on silica

反応条件: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A mixture of 2.8 g (0.01 mol) of 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 3.4 g (0.03 mol) of 2-ethylpiperazine in 15 ml of dimethylsulphoxide is heated at 140° C. for 2 hours. The solution is concentrated under a high vacuum, the residue is heated to 90° C. with 30 ml of water and the precipitate which has separated out is filtered off with suction, washed with methanol and water and isolated. 1.1 g (31% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(3-ethyl-1-piperazinyl)-3-quinolinecarboxylic acid monohydrate of decomposition point 255°-258° C. are obtained. The solution is concentrated under a high vacuum the residue is heated to 90° C. with 30 ml of water the precipitate which has separated out is filtered off with suction washed with methanol and water isolated