1-Methylpiperazine → HCID 13960204, compound

HRID 2413960Notes

Reaction equation

HRID 2413960 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([F:21])=[C:19](Cl)[C:12]3=[C:13]2[N:8]([CH:9]([CH3:23])[CH2:10][C:11]3=[O:22])[CH:7]=1)=[O:5])[CH3:2].[CH3:24][N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([F:21])=[C:19]([N:28]3[CH2:29][CH2:30][N:25]([CH3:24])[CH2:26][CH2:27]3)[C:12]3=[C:13]2[N:8]([CH:9]([CH3:23])[CH2:10][C:11]3=[O:22])[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 531671-MethylpiperazineHCID 13960199HCID 13960199, compound

Product 1

HCID 13960204HCID 13960204, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

16.89 g (0.05 mole) of 8-chloro-9-fluoro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was suspended in 300 ml of chloroform, 20.03 g (0.20 mole) of N-methylpiperazine was added thereto, and this mixture was stirred at 40°-50° C. for 4 hours. The resulting reaction solution was concentrated under reduced pressure and the residue thus obtained was purified by silica gel column chromatography [using a chloroform-methanol mixture (with a volume ratio of 10:1) as the developing solvent]. The fraction containing the desired product was evaporated to dryness under reduced pressure and the resulting residue was recrystallized from benzene to obtain 12.89 g (64.2% yield) of 9-fluoro-5-methyl-8-(4-methyl-1-piperazinyl)-6,7-dihydro 1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester in the form of yellow crystals.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. customthe residue thus obtained
  4. customwas purified by silica gel column chromatography [
  5. additionThe fraction containing the desired product
  6. customwas evaporated to dryness under reduced pressure
  7. customthe resulting residue was recrystallized from benzene

Sources & evidence

ORD record
ord-13e8e3ba862d48cf88f0a3c7d504db26
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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