Iodine → HCID 12733231, compound

Participants

Reaction Steps

A crystal of iodine followed by a few mls of a solution of 20.6 g of 2-fluorobenzyl chloride in 100 ml of ether is added to a suspension of 3.4 g of magnesium shavings in 50 ml of ether. Thereafter, the reaction is initiated via a hot air gun before adding dropwise, while maintaining the reaction at reflux, the remaining 2-fluorobenzyl chloride solution. After total addition, the reaction is maintained at reflux with stirring for an additional hour before successively adding 100 ml of ether and adding dropwise, with vigorous stirring, a solution of 25.0 g of N-benzyl-3-pyrrolidinone in 100 ml of ether. After complete addition, the resulting suspension is refluxed for an additional 2 hours, stirred at ambient temperature for 16 more hours, and then filtered. The filter cake is washed well with ether and then hydrolyzed by stirring in an ice-ammonium chloride solution. The aqueous solution is extracted thrice with ether and the combined ether extracts are washed successively with water and a sodium chloride solution and then dried. The solvent is removed and the residue is distilled at 135°-140° C., 0.1 mm pressure, to provide a viscous yellow oil which solidifies upon standing. The solid is recrystallized twice from an ethanol-water mixture to give the product, 1-benzyl-3-(2-fluorobenzyl)-3-pyrrolidinol, mp 75°-77° C.

Provenance & Evidence