2-Chloroquinoline → 2-{4-[(4-Chlorophenyl)sulfonyl]piperidin-1-yl}quinoline

HRID 1868064Notes

Reaction equation

HRID 1868064 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Cl[C:18]1[CH:27]=[CH:26][C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:19]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([CH:11]2[CH2:16][CH2:15][N:14]([C:18]3[CH:27]=[CH:26][C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[N:19]=3)[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 119282-ChloroquinolineHCID 81531DiisopropylethylamineHCID 27610724-[(4-Chlorophenyl)sulfonyl]piperidine

Product 1

HCID 685509392-{4-[(4-Chlorophenyl)sulfonyl]piperidin-1-yl}quinolineYield 8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure from Example 1A, 4-[(4-chlorophenyl)sulfonyl]piperidine (100 mg, 0.38 mmol) was reacted with 2-chloroquinoline (124 mg, 0.76 mmol), DIEA (0.27 ml, 1.52) and 1,4-dioxane (0.3 ml) at 190° C. to afford the title compound (11 mg), a white solid, in 8% yield.

Sources & evidence

ORD record
ord-1a23e12ed9ba4b0a8402336b13e5853f
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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