2-Methylpiperazine → 9-chloro-5-methyl-8-(3-methyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester

HRID 2413961Notes

Reaction equation

HRID 2413961 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([Cl: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][CH:25]1[CH2:30][NH:29][CH2:28][CH2:27][NH:26]1>C(#N)C>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2=[CH:17][C:18]([Cl:21])=[C:19]([N:29]3[CH2:28][CH2:27][NH:26][CH:25]([CH3:24])[CH2:30]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 660572-MethylpiperazineHCID 139602018,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester

Product 1

HCID 539147249-chloro-5-methyl-8-(3-methyl-1-piperazinyl)-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl esterYield 76.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

14.17 g (0.04 mole) of 8,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid ethyl ester was suspended in 250 ml of acetonitrile, 12.02 g (0.12 mole) of 2-methylpiperazine was added thereto, and this mixture was stirred at 50°-60° C. for 3 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 12.75 g (76.3% yield) of 9-chloro-5-methyl-8-(3-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-9478b80faa2f4d609bfca385648a8ec1
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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