1-(2-Hydroxyethyl)piperazine → HCID 12944895, compound

HRID 1578259Notes

Reaction equation

HRID 1578259 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1Cl)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18].[OH:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][OH:19])[CH2:23][CH2:24]1)[N:8]([CH2:13][CH3:14])[CH:7]=[C:6]([C:15]([OH:17])=[O:16])[C:5]2=[O:18]

Participants

4

Reactant 2

HCID 76771-(2-Hydroxyethyl)piperazineHCID 12733886HCID 12733886, compound

Product 1

HCID 12944895HCID 12944895, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

As described in Example 1, 4.3 g of 6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro-3-quinoline-carboxylic acid and 10.6 g of 1-(β-hydroxyethyl)-piperazine in 45 cm3 of DMSO (dimethylsulphoxide) were heated for 3 hours at 110° C. After evaporation of the solvent under a good vacuum, the viscous residue was taken up in 20 cm3 of isopropanol; the mixture was stirred and heated under reflux for 20 minutes. After standing for one night at 4° C., the solid was filtered off, washed with ethanol and recrystallised from methyl cellosolve (15 cm3). 3.5 g of 6-chloro-1-ethyl-7-[4-(β-hydroxyethyl)-piperazinyl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 215° C., were obtained.

Workup

  1. customAfter evaporation of the solvent under a good vacuum
  2. temperatureheated
  3. temperatureunder reflux for 20 minutes
  4. waitAfter standing for one night at 4° C.
  5. filtrationthe solid was filtered off
  6. washwashed with ethanol
  7. customrecrystallised from methyl cellosolve (15 cm3)

Sources & evidence

ORD record
ord-14dc1bb9bbf240e489859cd6de7d945d
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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