p-Toluenesulfonic acid → HCID 13607955, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 130 g (1.23 mole) of sodium bicarbonate and 145 g (1.32 mole) of thiophenol in 1.5 liters of dimethylformamide (which had stirred at room temperature for about 1 hr) was added 1-[(4-methylphenyl)sulfonyl]-3-piperidinemethanol ester with 4-methylbenzenesulfonic acid (the oil produced in Preparation 23) in 500 ml of dimethylformamide. The mixture was stirred at 80° C. for 12 hours and then at room temperature for 48 hr. One liter of dilute sodium hydroxide was added and the mixture was stirred for 2 hr. A viscous gum formed. The gum was separated and dissolved in methylene chloride. The resulting solution was extracted with several portions of dilute aqueous sodium hydroxide. The methylene chloride phase was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was recrystallized from diethyl ether-methylene chloride to give 221.4 g (72% based on starting 3-(hydroxymethyl)piperidine in Preparation 23) of white crystalline solid, m.p. 72°-75° C.

Provenance & Evidence