Piperazine → HCID 14052583, compound

HRID 330091Notes

Reaction equation

HRID 330091 reaction equation
[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10](F)[C:11]=2[CH3:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2].[NH:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1>CS(C)=O>[CH2:1]([N:3]1[C:12]2[C:7](=[CH:8][C:9]([F:15])=[C:10]([N:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[C:11]=2[CH3:13])[C:6](=[O:16])[C:5]([C:17]([OH:19])=[O:18])=[CH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 14052581HCID 14052581, compound

Product 1

HCID 14052583HCID 14052583, compoundYield 11.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of 1-ethyl-6,7-difluoro-1,4-dihydro-8-methyl-4-oxo-3-quinolinecarboxylic acid (350 mg), anhydrous piperazine (450 mg) in anhydrous DMSO (4 ml) was stirred at 50° to 72° C. for 18 hours. After the reacting mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography eluting chloroform-methanol-concentrated aqueous ammonia (20:6:1) to give the title compound (50 mg) as pale yellow flakes, mp 153°-156° C.

Workup

  1. concentrationAfter the reacting mixture was concentrated under reduced pressure
  2. customthe resulting residue was purified by silica gel column chromatography
  3. washeluting chloroform-methanol-concentrated aqueous ammonia (20:6:1)

Sources & evidence

ORD record
ord-00261fbfc46c490c8b8f8aebbaf754ef
Source dataset
uspto-grants-1990_01
Patent number
US04894458

Reaction notes

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