7-Chloro-4-(piperazin-1-yl)quinoline → HCID 178475084, compound

HRID 1353400Notes

Reaction equation

HRID 1353400 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[CH2:18]([O:20][NH:21][C:22]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=1)=S)[CH3:19].I([O-])(=O)(=O)=O.[Na+]>CN(C=O)C.O.O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([C:22](=[N:21][O:20][CH2:18][CH3:19])[NH:24][C:25]4[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=4)[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 7383897-Chloro-4-(piperazin-1-yl)quinolineHCID 21101975HCID 21101975, compoundHCID 23667635Sodium periodate

Product 1

HCID 178475084HCID 178475084, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Procedure

7-Chloro-4-(piperazin-1-yl)quinoline (124 mg, 0.5 mmol), N-ethoxy-N′-(4-fluorophenyl)thiourea (105 mg, 0.49 mmol), and sodium periodate (118 mg, 0.55 mmol) in DMF-water 1:1 (20 mL) are heated at 85° C. for 1 h. The reaction mixture is diluted with water and extracted with ether. The organic phase is dried (MgSO4) and concentrated. The residue is purified by column chromatography with hexane-EtOAc yielding the title product as pale yellow crystals.

Workup

  1. extractionextracted with ether
  2. dry with materialThe organic phase is dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography with hexane-EtOAc yielding the title product as pale yellow crystals

Sources & evidence

ORD record
ord-49aea1bd2fde4e789bb79c51bbd6b3b0
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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