Diphenylacetonitrile → alpha-(1-Cyclohexyl-3-azetidinyl)-alpha,alpha-diphenylacetonitrile

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Reaction Steps

To 191 g. (1.0 mole) of 1-cyclohexyl-3-azetidinol hydrochloride in methylene chloride was added a dilute sodium hydroxide solution, the organic layer was extracted, dried (sodium sulfate), filtered and concentrated in vacuo. The residue was dissolved in dry benzene and stirred with 116 g. (1.05 mole) of triethylamine and cooled with an ice bath. One mole (115 g.) of methanesulfonylchloride was added, dropwise, and stirring was continued at room temperature for 3 hours and the mixture was filtered. The filtrate was added at a fast dropwise rate to a reaction mixture of 50.0 g. (1 mole) of sodium hydride in 1 liter of dry toluene to which 193 g. (1 mole) of diphenylacetonitrile had been added slowly at 45°-50° C. and had already stirred at reflux for 2 hours. After addition was complete, reflux was continued for 2 hours, and the solution was stirred overnight. An equivalent amount of isooctane was added, and after extracting four times with a dilute hydrochloric acid solution, the acid layers were combined and made basic with 50% sodium hydroxide, with ice cooling, and extracted with chloroform. The organic layer was dried, filtered and concentrated in vacuo. The solid which formed when the residue was treated with isopropyl ether was recrystallized from isopropyl ether twice. The product weighed 58.0 g. (18% yield) and melted at 111°-114° C.

Provenance & Evidence