Piperazine → Norfloxacin

HRID 1416664Notes

Reaction equation

HRID 1416664 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH2:7]([N:9]1[C:18]2[C:13](=[CH:14][C:15]([F:20])=[C:16](Cl)[CH:17]=2)[C:12](=[O:21])[C:11]([C:22]([OH:24])=[O:23])=[CH:10]1)[CH3:8]>>[CH3:8][CH2:7][N:9]1[C:18]2[CH:17]=[C:16]([N:1]3[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]3)[C:15]([F:20])=[CH:14][C:13]=2[C:12](=[O:21])[C:11]([C:22]([OH:24])=[O:23])=[CH:10]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 4539Norfloxacin

Procedure

In Canadian patent 1,178,961 piperazine is condensed with 1-ethyl-6-fluoro-7-chloro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid to give norfloxacin. Canadian patent 1,214,466 claims the process of making the ester analogues of norfloxacin by the condensation of piperazine with the ester of the above compound. Hydrolysis of the ester leads to norfloxacin. Canadian patent 1,273,936 relates only to the synthesis of the quinolone carboxylic acid by cyclocondensation of a 2-benzoyl-3-amino-acrylonitrile followed by hydrolysis.

Sources & evidence

ORD record
ord-a9f45a1ee53b46da8747f9ab47b1457a
Source dataset
uspto-grants-1999_06
Patent number
US05914401

Reaction notes

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