4-Phenylpiperidin-4-ol → 2,2,2-Trifluoro-1-[6-(4-hydroxy-4-phenyl-piperidin-1-yl)-4-(4-methanesulfonyl-phenyl)-2-methyl-quinolin-3-yl]-ethanone

HRID 2104177Notes

Reaction equation

HRID 2104177 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH3:12])[C:6]([C:13](=[O:18])[C:14]([F:17])([F:16])[F:15])=[C:5]2[C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=1.[OH:29][C:30]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>>[F:15][C:14]([F:17])([F:16])[C:13]([C:6]1[C:7]([CH3:12])=[N:8][C:9]2[C:4]([C:5]=1[C:19]1[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:21][CH:20]=1)=[CH:3][C:2]([N:33]1[CH2:34][CH2:35][C:30]([OH:29])([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[CH2:31][CH2:32]1)=[CH:11][CH:10]=2)=[O:18]

Participants

3

Reactant 2

HCID 963874-Phenylpiperidin-4-olHCID 115400851-[6-Bromo-4-(4-methanesulfonyl-phenyl)-2-methyl-quinolin-3-yl]-2,2,2-trifluoro-ethanone

Product 1

HCID 675498522,2,2-Trifluoro-1-[6-(4-hydroxy-4-phenyl-piperidin-1-yl)-4-(4-methanesulfonyl-phenyl)-2-methyl-quinolin-3-yl]-ethanoneYield 17%

Procedure

The title compound was prepared from 1-[6-Bromo-4-(4-methanesulfonyl-phenyl)-2-methyl-quinolin-3-yl]-2,2,2-trifluoro-ethanone [example 24] and 4-hydroxy-4-phenylpiperidine according to the procedure of example 25, except that the reaction time was of 16 h. Yield: 17%; MS: m/z=569 (M+H).

Sources & evidence

ORD record
ord-d9e175e111164f65bed5df38cd41f625
Source dataset
uspto-grants-2009_08
Patent number
US07576217B2

Reaction notes

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