1-Methylpiperazine → Amifloxacin

HRID 2351023Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[F:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1Cl)[N:15]([NH:20][CH3:21])[CH:14]=[C:13]([C:22]([OH:24])=[O:23])[C:12]2=[O:25].[B:26]([F:29])([F:28])[OH:27]>CS(C)=O>[F:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)[N:15]([NH:20][CH3:21])[CH:14]=[C:13]([C:22]([OH:24])=[O:23])[C:12]2=[O:25].[B:26]([F:29])([F:28])[OH:27]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 6.87 g of 4-methyl-piperazine and 7.26 g of an anhydride of 6-fluoro-7-chloro-1-methylamino-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid and difluoroboric acid formed with 36 ml of dimethyl sulfoxide is stirred at 110° C. for 3 hours. As the reaction proceeds yellow crystals precipitate gradually from the reaction mixture. The anhydride of 6-fluoro-1-methylamino-7-(4-methyl-piperazino)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid and difluoroboric acid thus formed is hydrolyzed without isolation from the reaction mixture as follows:

Workup

customprecipitate gradually from the reaction mixture

Sources & evidence

ORD record: ord-1fe07ee62a794b34af40551accaf7279
Source dataset: uspto-grants-1989_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04871849

Reaction notes

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