1-Methylpiperazine → HCID 13116426, compound

HRID 2295724Notes

Reaction equation

HRID 2295724 reaction equation
Cl[C:2]1[C:11]([F:12])=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:16]([OH:18])=[O:17])=[C:8]3[S:15][CH2:14][CH2:13][N:9]32)=[CH:4][CH:3]=1.[CH3:20][N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>N1C=CC=CC=1>[F:12][C:11]1[C:2]([N:24]2[CH2:25][CH2:26][N:21]([CH3:20])[CH2:22][CH2:23]2)=[CH:3][CH:4]=[C:5]2[C:10]=1[N:9]1[CH2:13][CH2:14][S:15][C:8]1=[C:7]([C:16]([OH:18])=[O:17])[C:6]2=[O:19]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 13116425HCID 13116425, compound

Product 1

HCID 13116426HCID 13116426, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-Chloro-9-fluoro-5oxo-1,2-dihydro-5H-thiazolo(3,2-a)-quinoline-4-carboxylic acid (0.8 gram, 2.7 mmol) was dissolved in 5 ml of pyridine, then 2.7 grams (27 mmol) of N-methylpiperazine was added thereto, and the mixture was heated to reflux for forty eight hours. The content was concentrated under reduced pressure, water was added to the residue, and the insoluble matter was collected by filtration, washed with water, dried and recrystallized from dimethyl formamide to give 324 mg (42.0 percent) of the title compound, melting point 265° to 266° C. (decomposition). Elementary analyisis calculated as C17H18FN3O3S: C 56.19, H 4.99, N 11.56; Found: C 56.23, H 4.96, N 11.56.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for forty eight hours
  3. concentrationThe content was concentrated under reduced pressure, water
  4. additionwas added to the residue
  5. filtrationthe insoluble matter was collected by filtration
  6. washwashed with water
  7. customdried
  8. customrecrystallized from dimethyl formamide

Sources & evidence

ORD record
ord-0eb9bfbab71e4b9185b63603f9c639ce
Source dataset
uspto-grants-1984_01
Patent number
US04426381

Reaction notes

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