Piperazine → HCID 70487249, compound

HRID 463800Notes

Reaction equation

HRID 463800 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Cl:14])[C:11]=2[CH3:13])[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2].[NH:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN(C)P(N(C)C)(N(C)C)=O>[ClH:14].[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:11]=2[CH3:13])[C:6](=[O:15])[C:5]([C:16]([OH:18])=[O:17])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 134916997-Chloro-1-ethyl-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylic acid

Product 1

HCID 70487249HCID 70487249, compoundYield 48.3%

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
140 °C

Procedure

One hundred milliliter of hexamethylphosphoramide is added to a mixture of 5 g of 1-ethyl-7-chloro-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and 8.5 g of anhydrous piperazine, and the mixture is heated at 140° C. for 8 hours. After heating, the solvent is removed under reduced pressure and, after 500 ml of water is added to the resultant residue, the mixture is adjusted to pH 4 with glacial acetic acid and the insolubles are filtered out. The filtrate is concentrated under reduced pressure, resulting in a light yellow, solid substance. Recrystallization from isopropanol-water (2:1) mixture yields 3.2 g of 1-ethyl-7-(1-piperazinyl)-8-methyl-4-oxo-1,4-dihydroquinoline-3-carboxylic acid hydrochloride as the white, needle-like crystals. m.p. not less than 300° C.

Workup

  1. temperatureAfter heating
  2. customthe solvent is removed under reduced pressure
  3. additionafter 500 ml of water is added to the resultant residue
  4. filtrationthe insolubles are filtered out
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customresulting in a light yellow, solid substance
  7. customRecrystallization from isopropanol-water (2:1) mixture

Sources & evidence

ORD record
ord-85785997b2f0413c9cbdefaad5d7a508
Source dataset
uspto-grants-1985_10
Patent number
US04544747

Reaction notes

Loading…