Diisopropylethylamine → 3,5-Dichloro-4-{4-[(4-chlorophenyl)sulfonyl]piperidin-1-yl}pyridine

HRID 1868062Notes

Reaction equation

HRID 1868062 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:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([Cl:25])[C:23]=1Cl.CCN(C(C)C)C(C)C>O1CCOCC1>[Cl:17][C:18]1[CH:19]=[N:20][CH:21]=[C:22]([Cl:25])[C:23]=1[N:14]1[CH2:15][CH2:16][CH:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27610724-[(4-Chlorophenyl)sulfonyl]piperidineHCID 37865313,4,5-Trichloropyridine

Product 1

HCID 685523673,5-Dichloro-4-{4-[(4-chlorophenyl)sulfonyl]piperidin-1-yl}pyridineYield 33.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Using the procedure from Example 7A, 4-[(4-chlorophenyl)sulfonyl]piperidine (100 mg, 0.38 mmol) was reacted with 3,4,5-trichloropyridine (141 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 (51 mg), a white solid, in 33% yield.

Sources & evidence

ORD record
ord-51b7aa4676c94d3082e21a061ba04021
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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