Triethylamine → 7-Chloro-4-[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]quinoline

HRID 1353390Notes

Reaction equation

HRID 1353390 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]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.C(N(CC)CC)C>CCOC(C)=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:12]3[CH2:17][CH2:16][N:15]([S:25]([C:22]4[CH:23]=[CH:24][C:19]([F:18])=[CH:20][CH:21]=4)(=[O:27])=[O:26])[CH2:14][CH2:13]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95884-Fluorobenzenesulfonyl chlorideHCID 7383897-Chloro-4-(piperazin-1-yl)quinoline

Product 1

HCID 15067517-Chloro-4-[4-(4-fluorophenyl)sulfonylpiperazin-1-yl]quinoline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

7-Chloro-4-(piperazin-1-yl)quinoline (0.25 g, 1.0 mmol), 4-fluorobenzenesulfonyl chloride (0.23 g, 1.2 mmol), and triethylamine (349 μL, 2.5 mmol) are stirred at room temp. for 15 h. The reaction mixture is diluted with EtOAc, washed with water, dried (MgSO4), and concentrated. The residue is purified by column chromatography with hexane-EtOAc yielding the title product as a colorless solid.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is purified by column chromatography with hexane-EtOAc yielding the title product as a colorless solid

Sources & evidence

ORD record
ord-19767460b63c495daa8cf38ebc504508
Source dataset
uspto-grants-2007_05
Patent number
US07220856B2

Reaction notes

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