Piperidine → 3-Methanesulfonyl-2-methyl-4-phenyl-6-piperidin-1-yl-quinoline

HRID 13656Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([CH3:18])[C:12]([S:19]([CH3:22])(=[O:21])=[O:20])=[C:11]2[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1>O1CCOCC1.C(O)(C)(C)C.CCCCCCC.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:22][S:19]([C:12]1[C:13]([CH3:18])=[N:14][C:15]2[C:10]([C:11]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[CH:9][C:8]([N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1)=[CH:17][CH:16]=2)(=[O:21])=[O:20]

Participants

Conditions

Temperature: 120 °C

Procedure

A tube placed under argon was charged with tris(dibenzylideneacetone)dipalladium chloroform complex (3 mg), rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (3 mg) and cesium carbonate (121 mg, 0.37 mmol). 6-Bromo-3-methanesulfonyl-2-methyl-4-phenyl-quinoline (compound of example 2) (100 mg, 0.26 mmol) in dioxane/tert.-butanol 1:1 (15 ml) was added, followed by piperidine (0.027 ml, 0.031 mmol). The tube was sealed and heated at 120° C. for 2 h. The reaction mixture was cooled to 20° C., diluted with heptane, filtered through dicalite and purified directly by flash chromatography on silica gel in heptane/ethyl acetate 40:60 to give a yellow solid (47 mg, 46%). MS: m/z=381 (M+H).

Workup

customA tube placed under argon
customThe tube was sealed
temperatureThe reaction mixture was cooled to 20° C.
filtrationfiltered through dicalite
custompurified directly by flash chromatography on silica gel in heptane/ethyl acetate 40:60

Sources & evidence

ORD record: ord-0a71cd577b7c416b93536fca0d8d30da
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728142B2

Reaction notes

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