1-Methylpiperazine → HCID 12944919, compound

HRID 1578281Notes

Reaction equation

HRID 1578281 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])=[CH:8][N:9]2[CH2:12][CH2:13][OH:14])=[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]([CH2:12][CH2:13][OH:14])[CH:8]=[C:7]([C:15]([OH:17])=[O:16])[C:6]2=[O:18]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 12733881HCID 12733881, compound

Product 1

HCID 12944919HCID 12944919, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

28 g of 7-chloro-6-fluoro-1-(2-hydroxyethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, 40 g of 1-methyl piperazine and 200 cm3 of pyridine were heated for 18 hours under reflux. The solvent was removed by distillation under reduced pressure. The residue was taken up in 100 cm3 of water, the mixture was agitated and adjusted to pH 6.8 by the addition of acetic acid. The solid was filtered off, washed with water and recrystallised from DMF. 24 g of 6-fluoro-1-(2-hydroxyethyl)-7-(4-methyl-piperazinyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, m.p. 270° C., were obtained.

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed by distillation under reduced pressure
  3. additionadjusted to pH 6.8 by the addition of acetic acid
  4. filtrationThe solid was filtered off
  5. washwashed with water
  6. customrecrystallised from DMF

Sources & evidence

ORD record
ord-b60199b4b00c4edd8871aa71a991b8e0
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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