1-Methylpiperazine → HCID 13071763, compound

HRID 2418471Notes

Reaction equation

HRID 2418471 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH2:8]([O:10][C:11]([C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][C:18](Cl)=[C:19]([F:24])[CH:20]=2)[N:15]([CH:26]=[CH2:27])[CH:14]=1)=[O:12])[CH3:9]>N1C=CC=CC=1>[CH2:8]([O:10][C:11]([C:13]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][C:18]([N:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[C:19]([F:24])[CH:20]=2)[N:15]([CH:26]=[CH2:27])[CH:14]=1)=[O:12])[CH3:9]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 13071762HCID 13071762, compound

Product 1

HCID 13071763HCID 13071763, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1-Methylpiperazine (1.6 g) and 1-vinyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester (1.2 g) were added to a 3 ml of pyridine, and the mixture was refluxed for 5 hrs. The reaction mixture was concentrated in vacuo, water was added to the residue, and the mixture was adjusted to pH 4 with acetic acid. After filtering, the filtrate made alkali with sodium hydroxide solution. The crude crystals were recrystallized from a mixture of chloroform and benzene to give 1.0 g (68.5% yield) of 1-vinyl-6-fluoro-7-(4-methyl-1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester. mp: 186.5°-187.5° C.

Workup

  1. temperaturethe mixture was refluxed for 5 hrs
  2. concentrationThe reaction mixture was concentrated in vacuo, water
  3. additionwas added to the residue
  4. filtrationAfter filtering
  5. customThe crude crystals were recrystallized from a mixture of chloroform and benzene

Sources & evidence

ORD record
ord-e468255b662e403d9853c81eb1cffd77
Source dataset
uspto-grants-1984_09
Patent number
US04472579

Reaction notes

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