1-Methylpiperazine → HCID 12733914, compound

HRID 544222Notes

Reaction equation

HRID 544222 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl: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>O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl: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 12733886HCID 12733886, compound

Product 1

HCID 12733914HCID 12733914, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1-ethyl-6,7-dichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 2.86 g (0.01 mole), N-methylpiperazine 10 g (0.1 mole) and 15 ml water was heated in a sealed tube at 125°-130° C. (inner temperature) for 19 hours. After cooling, the reaction mixture was evaporated under vacuum and acidified with acetic acid. Insoluble matters were filtered off and the filtrate was neutralized with an aqueous solutiong of NaOH to pH 7, extracted with CHCl3, dried with anhydrous Na2SO4, and the solvent was distilled off. The residue was recrystallized from a mixed solvent of CHCl3 and benzene to give 1.05 g (30%) of 1-ethyl-6-chloro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid. Colorless needles.

Workup

  1. temperaturewas heated in a sealed tube at 125°-130° C. (inner temperature) for 19 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was evaporated under vacuum
  4. filtrationInsoluble matters were filtered off
  5. extractionextracted with CHCl3
  6. dry with materialdried with anhydrous Na2SO4
  7. distillationthe solvent was distilled off
  8. customThe residue was recrystallized from a mixed solvent of CHCl3 and benzene

Sources & evidence

ORD record
ord-acaa4dd7379e47b2a113b4193cc44c09
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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