Benzene → 1-Benzyl-4-(methoxymethyl)-N-phenylpiperidin-4-amine

Participants

Reaction Steps

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 dimethylsulfate at a temperature below 30° C. Upon completion, stirring is continued at room temperature, first for 2h. 30 and further, after the addition of a second portion of 2.6 parts of dimethyl sulfate, for 1h. 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.

Provenance & Evidence