1-Ethylpiperazine → 9-chloro-5-methyl-8-(4-ethyl-1-piperazinyl)-6,7-dihydro-1, 7-dioxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid

HRID 2413965Notes

Reaction equation

HRID 2413965 reaction equation
Cl[C:2]1[C:13]2=[C:14]3[N:9]([CH:10]([CH3:16])[CH2:11][C:12]2=[O:15])[CH:8]=[C:7]([C:17]([OH:19])=[O:18])[C:6](=[O:20])[C:5]3=[CH:4][C:3]=1[Cl:21].[CH2:22]([N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1)[CH3:23]>COCCO>[Cl:21][C:3]1[CH:4]=[C:5]2[C:14]3[N:9]([CH:8]=[C:7]([C:17]([OH:19])=[O:18])[C:6]2=[O:20])[CH:10]([CH3:16])[CH2:11][C:12](=[O:15])[C:13]=3[C:2]=1[N:27]1[CH2:28][CH2:29][N:24]([CH2:22][CH3:23])[CH2:25][CH2:26]1

Participants

4

Reactant 2

HCID 791961-EthylpiperazineHCID 201543468,9-dichloro-5-methyl-6,7-dihydro-1,7-dioxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid

Product 1

HCID 139602169-chloro-5-methyl-8-(4-ethyl-1-piperazinyl)-6,7-dihydro-1, 7-dioxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acidYield 80%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

3.26 g (0.01 mole) of 8, 9-dichloro-5-methyl-6, 7-dihydro-1,7-dioxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid was suspended in 30 ml of methyl cellosolve, 3.43 g (0.03 mole) of N-ethylpiperazine was added thereto, and this mixture was stirred at 100°-110° C. for 2 hours. The resulting reaction solution was evaporated to dryness under reduced pressure. 30 ml of methanol was added to the resulting residue and this mixture was stirred. The insoluble matter was collected by filtration and recrystallized from ethanol to obtain 3.23 g (80.0% yield) of 9-chloro-5-methyl-8-(4-ethyl-1-piperazinyl)-6,7-dihydro-1, 7-dioxo-1H, 5H-benzo[ij]quinolizine-2-carboxylic acid in the form of yellow crystals. These crystals had a melting point of 295°-298° C. (dec.).

Workup

  1. customThe resulting reaction solution
  2. customwas evaporated to dryness under reduced pressure
  3. addition30 ml of methanol was added to the resulting residue
  4. stirringthis mixture was stirred
  5. filtrationThe insoluble matter was collected by filtration
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-8a0d4a843a0443ddb0568aa126b83d8b
Source dataset
uspto-grants-1988_01
Patent number
US04720495

Reaction notes

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