Piperazine → Ciprofloxacin EP IMpurity B

HRID 637926Notes

Reaction equation

HRID 637926 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([N:19]4[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 133851637-Chloro-1-cyclopropyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 483178Ciprofloxacin EP IMpurity B

Procedure

Analogously to Example C, 7-chloro-1-cyclopropyl-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid is reacted with piperazine to give 1-cyclopropyl-1,4-dihydro-4-oxo-7-(piperazin-1-yl)-quinoline-3-carboxylic acid which decomposes at 298°-300° C. Preparation Examples for the end products according to the invention:

Sources & evidence

ORD record
ord-68faa4a807ed4abfb137b04a5ea04142
Source dataset
uspto-grants-1985_12
Patent number
US04559341

Reaction notes

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