Sodium Chloride → HCID 13640221, compound

HRID 225219Notes

Reaction equation

HRID 225219 reaction equation
C([Li])CCC.[CH3:6][O:7][C:8]1[CH:9]=[C:10](Br)[CH:11]=[CH:12][CH:13]=1.COC1C=C([Li])C=CC=1.[CH3:24][N:25]1[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]1.[Cl-].[Na+]>C(OCC)C.CCCCCC>[CH3:24][N:25]1[CH2:30][CH2:29][C:28]([OH:31])([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([O:7][CH3:6])[CH:9]=2)[CH2:27][CH2:26]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 169713-BromoanisoleHCID 740491-Methyl-4-piperidoneHCID 178418339ButyllithiumHCID 178506722HCID 178506722, compound

Product 1

HCID 13640221HCID 13640221, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

A solution of 159 ml. of n-butyl lithium 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 at which temperature it was stirred for one hour, thus providing 3-methoxyphenyllithium. 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 in dropwise fashion over a thirty minute period. Following the completion of the addition, the reaction mixture was stirred for two additional hours, and was then mixed with 50 ml. of saturated aqueous sodium chloride solution. The aqueous 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 formed in the above reaction.

Workup

  1. temperatureThe reaction mixture was chilled to 10° C.
  2. stirringstirred while a solution of 50 g
  3. additionthe completion of the addition
  4. stirringthe reaction mixture was stirred for two additional hours
  5. additionwas then mixed with 50 ml
  6. extractionThe aqueous solution was extracted several times with diethyl ether
  7. concentrationconcentrated to dryness
  8. customto provide 38 g

Sources & evidence

ORD record
ord-6f419be6a9de45f9a2a2e78519dd03ba
Source dataset
uspto-grants-1980_11
Patent number
US04236009

Reaction notes

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