Reaktion #56438

Reaktionsgleichung

dimethyl sulfate

dimethyl sulfate

4-(phenylamino)-1-(phenylmethyl)-4-piperidinemethanol

benzene

sodium hydroxide

→

4-(methoxymethyl)-N-phenyl-1-(phenylmethyl)-4-piperidinamine

Lösungsmittel

—

ice water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGUpon completion, stirring
2. 2
   workup.WAITfor 1 h
3. 3
   SonstigeThe organic phase is separated
4. 4
   Extraktionthe aqueous phase is extracted with benzene
5. 5
   WaschenThe combined organic phases are washed with water
6. 6
   Sonstigedried
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue is purified by column-chromatography over silica gel using
10. 10
    workup.ADDITIONa mixture of trichloromethane and 3% of methanol
11. 11
    SonstigeThe pure fractions are collected
12. 12
    Sonstigethe eluent is evaporated

Vorschrift

To a solution of 32 parts of 4-(phenylamino)-1-(phenylmethyl)-4-piperidinemethanol in 90 parts of benzene are added 0.2 parts of N,N,N-triethylbenzenemethanaminium chloride and 150 parts of a sodium hydroxide solution 60%. After stirring vigourously, there are added dropwise 10.9 parts of dimethyl sulfate at a temperature below 30° C. Upon completion, stirring is continued at room temerature, first for 2 h.30 and further, after the addition of a second portion of 2.6 parts of dimethyl sulfate, for 1 h.30. The reaction mixture is cooled in ice-water and 200 parts of water are added. The organic phase is separated and the aqueous phase is extracted with benzene. The combined organic phases are washed with water, dried, filtered and evaporated. The residue is purified by column-chromatography over silica gel using a mixture of trichloromethane and 3% of methanol, saturated with ammonia, as eluent. The pure fractions are collected and the eluent is evaporated, yielding 24.8 parts of 4-(methoxymethyl)-N-phenyl-1-(phenylmethyl)-4-piperidinamine as a residue.

Quelle