1-Methylpiperazine → Amifloxacin

HRID 615334Notes

Reaction equation

HRID 615334 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:14]([OH:16])=[O:15])=[CH:8][N:9]2[NH:12][CH3:13])=[CH:4][C:3]=1[F:18].[CH3:19][N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>COCCO>[F:18][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:23]1[CH2:24][CH2:25][N:20]([CH3:19])[CH2:21][CH2:22]1)[N:9]([NH:12][CH3:13])[CH:8]=[C:7]([C:14]([OH:16])=[O:15])[C:6]2=[O:17]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 30212917-Chloro-6-fluoro-1,4-dihydro-1-(methylamino)-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 55492Amifloxacin

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
127 °C

Procedure

The compound of Example 1 was prepared on a still larger scale as follows: A mixture of 970 g of 7-chloro-6-fluoro-1,4-dihydro-1-methylamino-4-oxo-3-quinolinecarboxylic acid, 1600 ml of N-methylpiperazine and 8 liters of 2-methoxyethanol was heated to reflux (about 127° C.) over a period of three hours. After 20 hours at reflux, the reaction mixture was cooled to 10° C. and filtered. The filter cake was washed with cold methoxyethanol, followed by methanol. The product was dried at 40° C., affording 925 g of 6-fluoro-1,4-dihydro-1-methylamino-7-(4-methyl-1-piperazinyl)-4-oxo-3-quinolinecarboxylic acid which was purified in the form of its methanesulfonate salt.

Workup

  1. temperaturewas heated
  2. temperatureAfter 20 hours at reflux
  3. temperaturethe reaction mixture was cooled to 10° C.
  4. filtrationfiltered
  5. washThe filter cake was washed with cold methoxyethanol
  6. customThe product was dried at 40° C.

Sources & evidence

ORD record
ord-1c1233a67d864c5784486f9319706e42
Source dataset
uspto-grants-1985_02
Patent number
US04499091

Reaction notes

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