Reaction #4015404
Related Literature (1)
openreactiondata ↗doi:10.1039/C8SC04228D
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a051825c44bf4bb09effd67c8191d7edNo renderable structure data available
CCC1CNCCN1Chemical Intermediate
Structures, identifiers and computed properties have been matched to the database record by CAS.
| Intermediates | 2-ethylpiperazine |
|---|---|
| IUPAC Name | — |
| CAS Number | 13961-37-0 |
| Database ID | 14094188 |
| Molecular Formula | — |
| Molecular Weight | — |
Product Information
2-ethylpiperazine (CAS 13961-37-0) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
Potential Applications
For professional research and industrial use only
Database ID 14094188
Safety Notice
For professional research and industrial use only. Review the supplier safety data sheet before handling.
Synthesis data
12 reactions · 12 references
Conditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a051825c44bf4bb09effd67c8191d7edConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-059ba121fc044fa49df729fc86ac8024Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-78f7b190477b4d38b364fbb4fdc6c8aeConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-6754a1187a3b4a899307bde4e87ed669Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-89e22c39ac504b78a1b1870b34dd925dConditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-89e22c39ac504b78a1b1870b34dd925dConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-a051825c44bf4bb09effd67c8191d7edConditions: temp:0.00; pressure:0.00; stir:
Source ID: ord-059ba121fc044fa49df729fc86ac8024Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-281c91867e344a1896f5d9a576cd628aConditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-7c96d3ff2ad8418eaedd3d4ce60d4812Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-3625c106dd5245cab2b9c32fbbe207a9Conditions: temp:140.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
Procedure: 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
Source ID: ord-f08ea848a335428e83fb1034649c55a8PubChem References
These sources are listed in the compound's public database record.
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