Piperazine → Ciprofloxacin

HRID 466252Notes

Reaction equation

HRID 466252 reaction equation
[NH:1]1[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17](F)[CH:18]=3)[C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]2)[CH2:9][CH2:8]1>O>[CH:7]1([N:10]2[C:19]3[C:14](=[CH:15][C:16]([F:21])=[C:17]([N:1]4[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]4)[CH:18]=3)[C:13](=[O:22])[C:12]([C:23]([OH:25])=[O:24])=[CH:11]2)[CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 2764CiprofloxacinYield 93.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

26.7 parts by weight of piperazine and 26.5 parts by weight of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid in 200 parts by volume of water are heated to 120° C. in an autoclave for 60 minutes and the mixture is then worked up as in Example 1. 30.9 parts by weight (93.4% of theory) of 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1piperazinyl)-3quinolinecarboxylic acid are obtained.

Sources & evidence

ORD record
ord-fb0ded2a33284c26994d8bb31e2cfede
Source dataset
uspto-grants-1992_10
Patent number
US05155223

Reaction notes

Loading…