Piperazine → Ethyl norfloxacin

HRID 2418464Notes

Reaction equation

HRID 2418464 reaction equation
N1C=CC=CC=1C.[NH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.[CH2:14]([O:16][C:17]([C:19]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][C:24](Cl)=[C:25]([F:30])[CH:26]=2)[N:21]([CH2:32][CH3:33])[CH:20]=1)=[O:18])[CH3:15]>>[CH2:14]([O:16][C:17]([C:19]1[C:28](=[O:29])[C:27]2[C:22](=[CH:23][C:24]([N:8]3[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]3)=[C:25]([F:30])[CH:26]=2)[N:21]([CH2:32][CH3:33])[CH:20]=1)=[O:18])[CH3:15]

Participants

4

Reactant 3

HCID 4837PiperazineHCID 79752-MethylpyridineHCID 12733855Ethyl 7-chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydro-3-quinolinecarboxylate

Product 1

HCID 12733941Ethyl norfloxacinYield 79%

Procedure

A mixture of 18 ml of picoline, 10.3 g of anhydrous piperazine, and 8.9 g of 1-ethyl-6-fluoro-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester was refluxed with stirring for 5 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was treated by the same manner described in Example 1 to give 8.2 g (79% yield) of 1-ethyl-6-fluoro-7-(1-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester. mp: 178°-180° C.

Workup

  1. temperaturewas refluxed
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was treated by the same manner

Sources & evidence

ORD record
ord-d0a50ed7aa694da786f5e71445db5909
Source dataset
uspto-grants-1984_09
Patent number
US04472579

Reaction notes

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