3-Bromoanisole → HCID 178506722, compound

HRID 1156995Notes

Reaction equation

HRID 1156995 reaction equation
C([Li:5])CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10](Br)[CH:11]=[CH:12][CH:13]=1>CCCCCC>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([Li:5])[CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 169713-BromoanisoleHCID 178418339Butyllithium

Product 1

HCID 178506722HCID 178506722, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A solution of 159 ml. of n-butyllithium in 100 ml. of hexane containing 47.7 g. of 3-methoxybromobenzene was stirred at -25° C. for twenty minutes and then was warmed to room temperature and stirred for one hour to provide 3-methoxyphenyl lithium. The reaction mixture was chilled to 10° C. and stirred while a solution of 50 g. of 1-methyl-4-piperidone in 100 ml. of diethyl ether was added dropwise over thirty minutes. Following complete addition, the reaction mixture was stirred for two hours, and then was diluted with 50 ml. of saturated aqueous sodium chloride solution. The solution was extracted several times with diethyl ether, and the ethereal extracts were combined and concentrated to dryness to provide 38 g. of 1-methyl-4-hydroxy-4-(3-methoxyphenyl)piperidine.

Sources & evidence

ORD record
ord-88bdb3e1ca7f4b668697dfba7c67fc9c
Source dataset
uspto-grants-1982_06
Patent number
US04337341

Reaction notes

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