1-Benzylpiperazine → HCID 12944896, compound

HRID 1578260Notes

Reaction equation

HRID 1578260 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].[CH2:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CS(C)=O>[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([C:11]2[CH:10]=[C:9]3[C:4]([C:5](=[O:18])[C:6]([C:15]([OH:17])=[O:16])=[CH:7][N:8]3[CH2:13][CH3:14])=[CH:3][C:2]=2[Cl:1])[CH2:28][CH2:27]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 759941-BenzylpiperazineHCID 12733886HCID 12733886, compound

Product 1

HCID 12944896HCID 12944896, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 4.3 g of 6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid and 10.5 g of 1-benzylpiperazine in 45 cm3 of DMSO was stirred and heated to 110° C. After 2 hours, the amount of Cl- ions in the reaction mixture corresponded to 94% of the amount calculated for the removal of one halogen atom. After evaporation of the solvent, the reaction product was isolated as in the preceding example; it was purified by recrystallisation from methyl cellosolve. 3.2 g of 7-(4-benzylpiperazinyl)-6-chloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid, m.p. 228° C., were obtained.

Workup

  1. customcalculated for the removal of one halogen atom
  2. customAfter evaporation of the solvent
  3. customit was purified by recrystallisation from methyl cellosolve

Sources & evidence

ORD record
ord-09a6f424b574420bbad17bd8f69d7351
Source dataset
uspto-grants-1981_09
Patent number
US04292317

Reaction notes

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