2-Methylpiperazine → Lomefloxacin

HRID 370716Notes

Reaction equation

HRID 370716 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([O:19]CC)=[O:18])=[CH:4]1)[CH3:2].[CH3:22][CH:23]1[CH2:28][NH:27][CH2:26][CH2:25][NH:24]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:27]3[CH2:26][CH2:25][NH:24][CH:23]([CH3:22])[CH2:28]3)[C:11]=2[F:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 660572-MethylpiperazineHCID 5140913Ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate

Product 1

HCID 3948LomefloxacinYield 56.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.50 g of ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate, 1.50 g of 2-methylpiperazine and 5 ml of pyridine was heated for 3 hours under reflux. The solvent of the reaction mixture was evaporated and the residue was dissolved in chloroform. The solution was washed with water, dried and evaporated. The residue was recrystallized from a mixture of benzene and isopropyl ether to give 1.00 g of the title compound as colorless needles, M.p. 126.5°-127.5° C.

Workup

  1. temperaturewas heated for 3 hours
  2. temperatureunder reflux
  3. customThe solvent of the reaction mixture was evaporated
  4. dissolutionthe residue was dissolved in chloroform
  5. washThe solution was washed with water
  6. customdried
  7. customevaporated
  8. customThe residue was recrystallized from a mixture of benzene and isopropyl ether

Sources & evidence

ORD record
ord-69e68f88a6c545f7beb8862b7961938f
Source dataset
uspto-grants-1985_07
Patent number
US04528287

Reaction notes

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