2-Methylpiperazine → Grepafloxacin

HRID 2271276Notes

Reaction equation

[CH3:1][CH:2]1[CH2:7][NH:6][CH2:5][CH2:4][NH:3]1.[CH:8]1([N:11]2[C:20]3[C:15](=[C:16]([CH3:23])[C:17]([F:22])=[C:18](F)[CH:19]=3)[C:14](=[O:24])[C:13]([C:25]([OH:27])=[O:26])=[CH:12]2)[CH2:10][CH2:9]1>CN1CCCC1=O>[CH:8]1([N:11]2[C:20]3[C:15](=[C:16]([CH3:23])[C:17]([F:22])=[C:18]([N:6]4[CH2:5][CH2:4][NH:3][CH:2]([CH3:1])[CH2:7]4)[CH:19]=3)[C:14](=[O:24])[C:13]([C:25]([OH:27])=[O:26])=[CH:12]2)[CH2:9][CH2:10]1

Participants

Conditions

Temperature: 90 °C

Procedure

0.65 g of 2-methylpiperazine was added to a solution of 0.48 g of 1-cyclopropyl-6,7-difluoro-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid in 5 ml of N-methyl-2-pyrrolidone, followed by heating at 90° C. for 20 minutes. After distilling off the solvent under reduced pressure, the residue was added with ethanol. The resulting crystals were filtered and recrystallized from ethyl acetate-ethanol to give 231 mg of 1-cyclopropyl-6-fluoro-7-(3-methyl-1-piperazinyl)-5-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

distillationAfter distilling off the solvent under reduced pressure
additionthe residue was added with ethanol
filtrationThe resulting crystals were filtered
customrecrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record: ord-0cf743d99f6147a3b5a4cbe9abea1817
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06333431B1

Reaction notes

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