Hydrochloric Acid → HCID 20431221, compound

Participants

Reaction Steps

57.6 g (0.5 mole) of 2,6-dimethylmorpholine hydrochloride, 95.2 g (0.5 mole) of p-tert.-butyl-propiophenone and 25 g (0.83 mole) of paraformaldehyde were heated under reflux in 200 ml of ethanol for 1 hour. After adding 0.7 ml of concentrated hydrochloric acid, the reaction mixture was stirred under reflux for a further 15 hours. It was then concentrated, the residue was taken up in chloroform and the chloroform mixture was washed twice with water, dried over sodium sulphate and concentrated. The solid residue was suspended in hot ethyl acetate, filtered off and dried. 47.6 g (30% of theory) of p-tert.-butyl-2-methyl-3-(2,6-dimethylmorpholin-4yl)-propionphenone hydrochloride were obtained and were dissolved in aqueous sodium bicarbonate solution and the solution and 25 g (0.83 mole) of paraformaldehyde were heated under reflux in 200 ml of ethanol for 1 hour. After adding 0.7 ml of concentrated hydrochloric acid, the reaction mixture was stirred under reflux for a further 15 hours. It was then concentrated, the residue was taken up in chloroform and the chloroform mixture was washed twice with water, dried over sodium sulphate and concentrated. The solid residue was suspended in hot ethyl acetate, filtered off and dried. 47.6 g (30% of theory) of p-tert.-butyl-2-methyl-3-(2,6-dimethylmorpholin-4yl)-propionphenone hydrochloride were obtained and were dissolved in aqueous sodium bicarbonate solution and the solution was then extracted with ethyl acetate and the product phase concentrated. A quantative yield of the free base of boiling point 145°-48° C./0.12 mm Hg column was obtained. ##STR59##

Provenance & Evidence