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

HRID 1868070Notes

Reaction equation

HRID 1868070 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl[C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:22]=1.CCN(C(C)C)C(C)C>O1CCOCC1>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([CH:14]2[CH2:15][CH2:16][N:17]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[CH2:18][CH2:19]2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 119282-ChloroquinolineHCID 81531DiisopropylethylamineHCID 185386364-[(4-Tert-butylphenyl)sulfonyl]piperidine

Product 1

HCID 685480072-{4-[(4-Tert-butylphenyl)sulfonyl]piperidin-1-yl}quinolineYield 18%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure from Example 7A, 4-[(4-tert-butylphenyl)sulfonyl]piperidine (150 mg, 0.53 mmol) was reacted with 2-chloroquinoline (175 mg, 1.06 mmol), DIEA (0.37 ml, 2.12) and 1,4-dioxane (0.2 ml) at 185° C. to afford the title compound (39 mg), a white solid, in 18% yield.

Sources & evidence

ORD record
ord-046085e83c6841848bfcdc0f7ab1a11e
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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