1-Ethylpiperidin-4-one → 1-Ethyl-4-(2-fluoro-3-(methylthio)phenyl)piperidin-4-ol

HRID 2358149Notes

Reaction equation

HRID 2358149 reaction equation
C([Li])CCCCC.Br[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([S:15][CH3:16])[C:10]=1[F:17].[CH2:18]([N:20]1[CH2:25][CH2:24][C:23](=[O:26])[CH2:22][CH2:21]1)[CH3:19]>O1CCCC1>[CH2:18]([N:20]1[CH2:25][CH2:24][C:23]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([S:15][CH3:16])[C:10]=2[F:17])([OH:26])[CH2:22][CH2:21]1)[CH3:19]

Participants

5

Reactant 3

HCID 771591-Ethylpiperidin-4-oneHCID 574480643-Bromo-2-fluorothioanisoleHCID 178506865HCID 178506865, compound2×

Product 1

HCID 574480791-Ethyl-4-(2-fluoro-3-(methylthio)phenyl)piperidin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation according to preparation 1 with the exception that n-hexyllitium was used instead of n-butyllithium: 1-bromo-2-fluoro-3-(methylthio)benzene (15 g, 67.8 mmol), dry tetrahydrofurane (70 ml), n-hexyllithium (2.3 M in hexane, 31 ml, 71 mmol), 1-ethylpiperidin-4-one (9.06 g, 71 mmol). Yield: 20.7 g. MS m/z (rel. intensity, 70 eV) 269 (M+, 49), 254 (bp), 236 (36), 56 (31), 84 (23).

Workup

  1. customPreparation

Sources & evidence

ORD record
ord-b73a5bdbef504a27949d776206f86ba3
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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