1-Methylpiperazine → 7-Fluoro-8-(4-methyl-1-piperazinyl)-5-oxo-1,2-dihydro-5H-thiazolo (3,2-a)-quinoline-4-carboxylic acid

HRID 2295726Notes

Reaction equation

HRID 2295726 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[C:8]3[S:14][CH2:13][CH2:12][N:9]32)=[CH:4][C:3]=1[F:19].[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[F:19][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[N:24]1[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]1)[N:9]1[CH2:12][CH2:13][S:14][C:8]1=[C:7]([C:15]([OH:17])=[O:16])[C:6]2=[O:18]

Participants

4

Reactant 2

HCID 531671-Methylpiperazine2×HCID 104700458-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)quinoline-4-carboxylic acid

Product 1

HCID 100672737-Fluoro-8-(4-methyl-1-piperazinyl)-5-oxo-1,2-dihydro-5H-thiazolo (3,2-a)-quinoline-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1 gram (3.3 mmol) of 8-chloro-7-fluoro-5-oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid, 1.65 g. (0.0165 mol) of N-methylpiperazine and 20 ml of pyridine was heated to reflux. After twelve hours, 1.65 g. (0.0165 mol) of N-methylpiperazine was added thereto again and the heating to reflux was continued for twelve hours. When the reaction was completed, the mixture was allowed to cool to a room temperature, crystals separated out therefrom were collected by filtration, washed with pyridine and ether and air dried to give the title compound. Yellow powdery crystals. Yield 720 mg (60 percent).

Workup

  1. waitAfter twelve hours
  2. temperatureagain and the heating to reflux
  3. waitwas continued for twelve hours
  4. customcrystals separated out
  5. filtrationtherefrom were collected by filtration
  6. washwashed with pyridine and ether and air
  7. customdried

Sources & evidence

ORD record
ord-e31794cf468b4e70ae4e198386b95605
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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