7-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 1-Ethyl-6-fluoro-1,4-dihydro-7-[3-(hydroxymethyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid, hydrochloride

HRID 248461Notes

Reaction equation

HRID 248461 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][NH:7][CH2:6][CH2:5][NH:4]1.[Cl:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14](=[O:25])[C:15]([C:22]([OH:24])=[O:23])=[CH:16][N:17]2[CH2:20][CH3:21])=[CH:12][C:11]=1[F:26]>N1C=CC=CC=1>[ClH:9].[CH2:20]([N:17]1[C:18]2[C:13](=[CH:12][C:11]([F:26])=[C:10]([N:7]3[CH2:6][CH2:5][NH:4][CH:3]([CH2:2][OH:1])[CH2:8]3)[CH:19]=2)[C:14](=[O:25])[C:15]([C:22]([OH:24])=[O:23])=[CH:16]1)[CH3:21]

Participants

4

Reactant 2

HCID 4831697-Chloro-1-ethyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 11788288(Piperazin-2-yl)methanol

Product 1

HCID 148393971-Ethyl-6-fluoro-1,4-dihydro-7-[3-(hydroxymethyl)-1-piperazinyl]-4-oxo-3-quinolinecarboxylic acid, hydrochloride

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 2 g of 2-hydroxymethylpiperazine, 1 g of 7-chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid and 8 ml of pyridine was heated at 130° C. in a sealed bottle, under argon, overnight. The solvent was removed and the residue adsorbed onto silica gel, then added to a column of flash grade silica gel. The column was eluted with methanol:water (95:5). The product fraction was collected, dissolved in methanoldichloromethane and converted to the hydrochloride salt, mp>275° C.

Workup

  1. customThe solvent was removed
  2. additionadded to a column of flash grade silica gel
  3. washThe column was eluted with methanol:water (95:5)
  4. customThe product fraction was collected
  5. dissolutiondissolved in methanoldichloromethane

Sources & evidence

ORD record
ord-0e7d464895b94570a0d7b9c91f1bdccd
Source dataset
uspto-grants-1993_05
Patent number
US05210193

Reaction notes

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