7-Chloro-4-(piperazin-1-yl)quinoline → HCID 178502862, compound

HRID 1353402Notes

Reaction equation

HRID 1353402 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.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:26]([NH:28][O:29][CH3:30])=S)=[CH:21][CH:20]=1.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:26](=[N:28][O:29][CH3:30])[NH:25][C:22]4[CH:21]=[CH:20][C:19]([F:18])=[CH:24][CH:23]=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 21101973HCID 21101973, compoundHCID 23667635Sodium periodate

Product 1

HCID 178502862HCID 178502862, compound

Reagents, catalysts & solvents 2

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

Procedure

7-Chloro-4-(piperazin-1-yl)quinoline (297 mg, 1.2 mmol), N-(4-Fluorophenyl)-N′-methoxythiourea (240 mg, 1.2 mmol), and sodium periodate (278 mg, 1.3 mmol) in DMF-water 1:1 (40 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.

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

Sources & evidence

ORD record
ord-1a7ff1c4d8314b9d83859f37678ba419
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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