Piperazine → HCID 4594465, compound

HRID 1284511Notes

Reaction equation

HRID 1284511 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[NH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1>CS(C)=O>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([N+:19]([O-:21])=[O:20])=[C:2]([N:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[CH:11]=3)[C:6](=[O:18])[C:7]([C:15]([OH:17])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 4837PiperazineHCID 13385162HCID 13385162, compound

Product 1

HCID 4594465HCID 4594465, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 9.3 g (0.03 mol) of 7-chloro-1-cyclopropyl-1,4-dihydro-6-nitro-4-oxo-3-quinolinecarboxylic acid and 12.9 g (0.15 mol) of piperazine is warmed at 120° C. in 60 ml of dimethylsulphoxide for 15 minutes. After a short time, a precipitate separates out from the hot solution. The mixture is concentrated under a high vacuum, the residue is stirred with 30 ml of water and the mixture is heated again at 95° C. for 30 minutes. The mixture is brought to pH 8 with 2N hydrochloric acid, and the precipitate is filtered off with suction and washed with water and methanol. 5.8 g (54% of theory) of 1-cyclopropyl-1,4-dihydro-6-nitro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid of decomposition point 296°-298° C. are isolated.

Workup

  1. concentrationThe mixture is concentrated under a high vacuum
  2. filtrationthe precipitate is filtered off with suction
  3. washwashed with water and methanol

Sources & evidence

ORD record
ord-e858c3ec3d464fcdbaff8066ffac277c
Source dataset
uspto-grants-1986_01
Patent number
US04563459

Reaction notes

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