1-Methylpiperazine → HCID 12733892, compound

HRID 544236Notes

Reaction equation

HRID 544236 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Br:14])=[C:10](Cl)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Br:14])=[C:10]([N:23]3[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]3)[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 12733873HCID 12733873, compound

Product 1

HCID 12733892HCID 12733892, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1-ethyl-6-bromo-7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 1.65 g, N-methylpiperazine 2.5 g and pyridine 2 ml was refluxed for 12 hours by heating. The reaction mixture was evaporated under vacuum. The residue was dissolved in an aqueous solution of acetic acid to separate insoluble matters by filtration and neutralized with an aqueous solution of NaOH. The precipitated crystals were collected by filtration and dried. Recrystallizing the precipitates from a mixed solvent of DMF and ethanol, 1.45 g (74%) of 1-ethyl-6-bromo-1,4-dihydro-7-(4-methyl-1-piperazinyl)-4-oxoquinoline-3-carboxylic acid was obtained as colorless needle crystals.

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperatureby heating
  3. customThe reaction mixture was evaporated under vacuum
  4. dissolutionThe residue was dissolved in an aqueous solution of acetic acid
  5. customto separate insoluble matters
  6. filtrationby filtration
  7. filtrationThe precipitated crystals were collected by filtration
  8. customdried
  9. customRecrystallizing the
  10. customprecipitates from a mixed solvent of DMF and ethanol

Sources & evidence

ORD record
ord-7994185421394b1b9fb0886a012b28bb
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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