Norfloxacin → HCID 68461411, compound

HRID 901111Notes

Reaction equation

HRID 901111 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:19])=[C:10]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2].C(N([CH2:29][CH3:30])CC)C.C([CH:33](Cl)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=C>O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:19])=[C:10]([N:13]3[CH2:18][CH2:17][N:16]([CH2:33][C:34]4[CH:39]=[CH:38][C:37]([CH:29]=[CH2:30])=[CH:36][CH:35]=4)[CH2:15][CH2:14]3)[CH:11]=2)[C:6](=[O:20])[C:5]([C:21]([OH:23])=[O:22])=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 4539NorfloxacinHCID 8471TriethylamineHCID 11768772Benzene, 1-(chloromethyl)-3(or 4)-ethenyl-

Product 1

HCID 68461411HCID 68461411, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under a nitrogen atmosphere, 400 mg (1.252 mmol) of 1-ethyl-6-fluoro-1,4-dihydro-7-(1-piperazinyl)-4-oxo-3-quinoline carboxylic acid were mixed with 0.349 ml (2.505 mmol) of triethylamine in a round flask of 50 ml and stirred at room temperature for 10 minutes. While the temperature of the inside of the container was kept at −10° C., 0.177 ml (1.252 mmol) of vinylbenzylchloride was slowly dripped thereinto. Under a nitrogen atmosphere, the reaction was conducted for three hours while keeping the temperature at −10° C., and then distilled water was added to the reactants which were then extracted with dichloromethane. The extracts were concentrated and then chromatographed (20 gm silica, 5% MeOH/CH2Cl2) to give 501 mg (91.9%) of 1-ethyl-6-fluoro-1,4-dihydro-7-[4-(4-vinylbenzyl)-1-piperazinyl]-4-oxo-3-quinoline carboxylic acid.

Workup

  1. customwas kept at −10° C.
  2. waitUnder a nitrogen atmosphere, the reaction was conducted for three hours
  3. customat −10° C.
  4. extractionwere then extracted with dichloromethane
  5. concentrationThe extracts were concentrated
  6. customchromatographed (20 gm silica, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-7edff0153fcc4029963f7e700d37249a
Source dataset
uspto-grants-2008_04
Patent number
US07361719B2

Reaction notes

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