Diisopropylethylamine → 1-{4-[(4-Chlorophenyl)sulfonyl]piperidin-1-yl}isoquinoline

HRID 1868063Notes

Reaction equation

HRID 1868063 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[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:21]=[CH:20][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[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:21]=[CH:20][N:19]=3)[CH2:13][CH2:12]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 140539Isoquinoline, 1-chloro-HCID 27610724-[(4-Chlorophenyl)sulfonyl]piperidine

Product 1

HCID 685537781-{4-[(4-Chlorophenyl)sulfonyl]piperidin-1-yl}isoquinolineYield 10.2%

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 1-chloroisoquinoline (131 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 (15 mg), an off-white solid, in 10% yield.

Sources & evidence

ORD record
ord-1c25ab4801574beca6fee254b9b0b865
Source dataset
uspto-grants-2009_12
Patent number
US07632838B2

Reaction notes

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