p-Toluenesulfonic acid → HCID 20217759, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 57.92 g (0.504 mole) of 2-hydroxymethylpiperidine and 236 g (1.24 mole) of tosylchloride in one liter of pyridine was stirred at 25° C. overnight. The mixture was quenched in water and the aqueous mixture was extracted with several portions of methylene chloride. The combined methylene chloride extract was extracted with 1M sulfuric acid solution followed by 1M aqueous sodium hydroxide, dried over magnesium sulfate and evaporated to give an oil which was shown by NMR and mass spectrometry to be 1-[(4-methylphenyl)sulfonyl]-2-piperidinemethanol ester with 4-methylbenzene sulfonic acid. A mixture of 40.78 g (0.0964 mole) of the oil, 24.60 g (0.171 mole) of p-chlorothiophenol and 25.4 g of sodium carbonate in 200 ml of dimethylformamide was stirred at 100° C. overnight and then quenched in dilute sodium hydroxide. The mixture was extracted with several portions of methylene chloride. The combined extract was extracted with several portions of 1M sodium hydroxide, dried over magnesium sulfate and evaporated in vacuo to give an oil. The oil was crystallized from ether-hexane to give 29.73 g of the solid product. On standing at room temperature, the solid melted.

Provenance & Evidence