Coben ,Takeda, Japan,1971
To a simultaneously stirred and refluxed suspension of 5.6 parts by weight of sodamide in 60 parts by volume of anhydrous toluene, there is added dropwise a solution of 18.4 parts by weight of N-(2-pyridylmethyl)aniline in 20 parts by volume of anhydrous toluene. After the addition is complete, the mixture is refluxed for two hours under constant stirring.
To the resulting mixture there is added dropwise a solution of 14.9 parts by weight of 2-piperidinoethyl chloride in 20 parts by volume of anhydrous toluene and the whole mixture is stirred and refluxed for another two hours. After cooling, water is added carefully to decompose the unreacted sodamide, the separated toluene layer is dried over anhydrous sodium sulfate and the solvent removed under reduced pressure.
The residual oil is subjected to distillation under reduced pressure, the fraction boiling in the range of 185°C to 198°C/4 mm Hg being collected. Purification of the fraction by redistillation under reduced pressure gives 22.5 parts by weight of N-(2-piperidinoethyl)-N-(2-pyridylmethyl)-aniline which boils at 195°C to 196°C/4 mm Hg. Yield 76.3%.
