Piperazine → HCID 70495615, compound

HRID 544235Notes

Reaction equation

HRID 544235 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Br:14])=[C:10]([Cl:13])[CH:11]=2)[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>N1C=CC=CC=1>[ClH:13].[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([Br:14])=[C:10]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH:11]=2)[C:6](=[O:15])[CH:5]([C:16]([OH:18])=[O:17])[CH2:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 12733873HCID 12733873, compound

Product 1

HCID 70495615HCID 70495615, compoundYield 67%

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, piperazine 2.15 g and pyridine 2 ml was refluxed for 12 hours by heating. The reaction mixture was evaporated under vacuum and dissolved in aqueous acetic acid. The insoluble matters were removed by filtration. The filtrate was neutralized with an aqueous solution of NaOH. The precipitated crystals were collected by filtration and washed with water. The precipitate was recrystallized from a mixed solvent of concentrated hydrochloric acid and ethanol to obtain 1.4 g (67%) of 1-ethyl-6-bromo-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid hydrochloride as colorless needles.

Workup

  1. temperaturewas refluxed for 12 hours
  2. temperatureby heating
  3. customThe reaction mixture was evaporated under vacuum
  4. dissolutiondissolved in aqueous acetic acid
  5. customThe insoluble matters were removed by filtration
  6. filtrationThe precipitated crystals were collected by filtration
  7. washwashed with water
  8. customThe precipitate was recrystallized from a mixed solvent of concentrated hydrochloric acid and ethanol

Sources & evidence

ORD record
ord-2bf06bfb9dcd4da9a96ccf5fa76a5bba
Source dataset
uspto-grants-1984_05
Patent number
US04448962

Reaction notes

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