Duvadilan,Duphar,France,1958
To a solution of 30.7 g (0.203 mol) of 1-phenoxy-2-aminopropane in 150 ml
of ethanol there was added 31.9 g (0.100 mol) of 1-(4'-benzyloxyphenyl)-2-
bromopropanone-1. The mixture was heated to boiling temperature and the
solution was then refluxed in a reflux condenser for 3 hours. Most of the
ethanol was then distilled off in vacuo, Then to the residue there was addedabout 150 ml of diethyl ether. The hydrogen bromide salt of 1-phenoxy-2-
aminopropane was filtered off and washed with diethyl ether.
The collected ethereal filtrates were acidified with 50 ml of 4 N hydrochloric
acid and this solution was stirred vigorously. The hydrochloride of 1-(4'-
benzyloxyphenyl)-2-(1'-methyl-2-phenoxy-ethylamino)propanone-1
precipitated out, was filtered off, washed with water and then with diethyl
ether. Then this substance was dried in vacuo. The yield was 37.7 g, i.e., 89%
of the theoretically possible yield, calculated on 1-(4'-benzyloxyphenyl)-2-
bromine propanone-1. This substance had a light yellow color and melted at
197 to 198°C, while decomposing.
Then 21.89 g of the hydrochloride salt was dissolved in 600 ml of 80%
aqueous ethanol. With the addition of a palladium carbon catalyst, this
solution was hydrogenated at room temperature under a hydrogen pressure of
about 1.1 atmospheres. After 2 mols hydrogen had been absorbed, the
catalyst was filtered off and the filtrate was evaporated in vacuo until
crystallization occurred. Then the crystals were dissolved by heating in the
smallest possible quantity of water and after cooling, the crystallized
substance was filtered off, washed with water and dried in vacuo. The yield
was 6.80 g, i.e., 39% of the theoretically possible yield. The resultant product
recrystallized from water melted at 203° to 204°C.
