Iodoethane → HCID 13423965, compound

Participants

Reaction Steps

Sodium hydride, 3.44 g (0.0816 mole) in 57% mineral oil suspension was washed three times with petroleum ether (30°-60° C.) under nitrogen atmosphere, suspended in 60 ml of freshly distilled anhydrous dimethylformamide and treated slowly with a solution of 24.3 g (0.0742 mole) of 1-benzyl-3-(2-ethoxyphenoxy)methyl-3-pyrrolidinol in 60 ml of freshly distilled anhydrous dimethylformamide. After hydrogen evolution had ceased, a solution of 11.6 g (0.0742 mole) of ethyl iodide in 60 ml of freshly distilled anhydrous dimethylformamide was added dropwise under a nitrogen atmosphere. The reaction mixture was stirred at room temperature for 16 hours (overnight), then cautiously diluted with 50 ml of water and poured into 1500 ml of water. The suspension was extracted with chloroform (3×200 ml) and the combined chloroform extracts washed with water (3×200 ml), dried over magnesium sulfate and evaporated under reduced pressure (26.1 g). The crude product which contained starting material was dissolved in benzene and chromatographed on a 500 g column of florisil packed in benzene. The column was eluted with benzene and methanol-benzene solvent mixtures. The fractions containing product were combined and evaporated under reduced pressure. Weight of residue was 15.0 g (57%). A mixture of 3.0 g (0.0084 mole) of the product and 1.06 g (0.0084 mole) of oxalic acid dihydrate in isopropanol was warmed to solution, filtered, and the filtrate seeded. The oxalate salt, 3.4 g, was collected by filtration, m.p. 125°-127° C. The material was recrystallized twice from isopropanol-isopropyl ether leaving 0.8 g of salt, m.p. 127°-129° C., which did not analyze as expected. The filtrate gave a second crop, 1.0 g, m.p. 125°-127° C. which was dried at 62° C. and 0.01 mm pressure for 4 hours and at room temperature and 0.01 mm pressure overnight.

Provenance & Evidence