2-Methylpiperazine → Lomefloxacin

HRID 370714Notes

Reaction equation

HRID 370714 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]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[CH3:20][CH:21]1[CH2:26][NH:25][CH2:24][CH2:23][NH:22]1>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:25]3[CH2:24][CH2:23][NH:22][CH:21]([CH3:20])[CH2:26]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 98351791-Ethyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 3948LomefloxacinYield 27.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.00 g of 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 1.10 g of 2-methylpiperazine and 10 ml of pyridine was heated for 15 minutes under reflux. The reaction mixture was evaporated and methanol was added to the residue. The precipitate was filtered and recrystallized from ethanol to give 0.36 g of the title compound as colorless needles, M.p. 239°-240.5° C.

Workup

  1. temperaturewas heated for 15 minutes
  2. temperatureunder reflux
  3. customThe reaction mixture was evaporated
  4. additionmethanol was added to the residue
  5. filtrationThe precipitate was filtered
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-f922b1f6e527486d953d180ce3cc4055
Source dataset
uspto-grants-1985_07
Patent number
US04528287

Reaction notes

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