Diethyl Ether → HCID 70578049, compound

Participants

Reaction Steps

A mixture of 8.00 g (0.029 mole) of N-formyl-4-diphenylmethylpiperidine and 3.61 g (2.67 ml, 0.029 mole) of dimethylsulfate was heated on a steam bath for two hours to give a clear thick syrup. To this material was then added 1.38 g (2.00 ml, 0.031 mole) of ethylamine in 15 ml of methylene chloride. The resulting solution was stirred for 1.5 hours at 25°, stripped, slurried in ether, and treated with 28 ml of 3 N sodium hydroxide solution. The ethereal layer was dried over potassium carbonate, filtered through diatomaceous earth filter aid and evaporated to give 8.77 g of yellow liquid. Treatment of this material in isopropanol with 3.26 g of oxalic acid dihydrate afforded 5.0 g of white solid m.p. 165°-175° C. Recrystallization from isopropanol afforded pure 4-(diphenylmethyl)-1-N-ethyliminomethylpiperidine oxalate hemihydrate as a white solid; m.p. 185°-187° C.

Provenance & Evidence