Piperazine → HCID 23499079, compound

HRID 1836201Notes

Reaction equation

HRID 1836201 reaction equation
[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](F)[CH:12]=2)[C:7](=[O:15])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]1)[CH:2]=[CH2:3].[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1>CN(C)C=O.CO>[CH2:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:12]=2)[C:7](=[O:15])[C:6]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 4837PiperazineHCID 1479570HCID 1479570, compound

Product 1

HCID 23499079HCID 23499079, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 1-allyl-7-fluoro-4-quinolone-3-carboxylate (390 mg, 1.41 mmol) and piperazine (1.22 g, 14.1 mmol) in dry N,N-dimethylformamide was heated for 7 hours at 110° C., then stirred at room temperature for 2 days. The solvent was evaporated to dryness, and the residue was purified by column chromatography on silica gel using dichloromethane:methanol (gradient from 98:2 to 85:15) as eluent affording 300 mg (62% yield) of ethyl 1-allyl-4-oxo-7-(4-piperazinyl)quinoline-3-carboxylate.

Workup

  1. customThe solvent was evaporated to dryness
  2. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-8937237c56314275ab4562d496d6d88f
Source dataset
uspto-grants-2004_08
Patent number
US06777420B2

Reaction notes

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