Hexane → HCID 22447278, compound

Participants

Reaction Steps

To the so obtained aqueous thiolcarbamic acid salt solution was added 7.2 kg (179 moles) of 40% sodium hydroxide at 50° to 60° C., following which 27.6 kg (179 moles) of α,α-dimethylbenzyl chloride was added dropwise at the same temperature over the course of 20 minutes. After repeating this operation four times, a further addition dropwise of 69.0 kg (447 moles) of α,α-dimethylbenzyl chloride was made over the course of 30 minutes. The reaction mixture was then stirred at 50° to 60° C. for 1.5 hours to complete the reaction. The pH of the system ranged from 9.5 to 12.5 during the reaction. After cooling the reaction mixture, 80 liters of hexane was added, and the organic layer and the aqueous layer were separated. The organic layer was then washed with 80 liters of 2% hydrochloric acid and 80 liters of water. After distilling the hexane off from this hexane solution, a 0.5 liter ethanol solution of 0.5 kg of p-toluenesulfonic acid was added, and the mixture was reacted and distilled under reduced pressure (10 to 20 mm Hg) at below 110° C. The intended N-(α,α-dimethylbenzylthio-carbonyl)piperidine (93 kg) was obtained in the residue. On analysis by gas chromatography, this product was found to have a purity of 96.0%, and its yield based on thiolcarbamic acid salt was 78.5%. The melting point was 34.5°-36.0° C.

Provenance & Evidence