Potassium Iodide → HCID 20512453, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 28.2 g (0.143 moles) of N-(β-chloropropyl)-2,6-dimethylaniline, prepared as described in Example 3, Method (b), point (a), 36.4 g (0.285 moles) of 4-chloroaniline and 1.6 g (10 mmoles) of potassium iodide is stirred at 140° to 145° C. for 3 hours under nitrogen atmosphere. The mixture is allowed to cool to about 60° C., and 30 ml of ethyl acetate are added. The mixture is cooled to room temperature, and the separated precipitate is filtered off, washed with ethyl acetate and dried. 14.0 g of 1-(2',6'-dimethyl-phenylamino)-2-(4'-chlorophenyl-amino)-propane hydrochloride (fraction A) are obtained. The filtrate is acidified with isopropanolic hydrochloric acid (acid content: about 15 g/100 ml), the separated precipitate is filtered off, washed with isopropanol and dried. 28.8 g of the same compound (fraction B) are obtained. Fractions A and B are combined, triturated with 100 ml of water, filtered, washed with water, dried, and the resulting solid, weighing 25.7 g, is recrystallized from methanol. 21.4 g (46.0%) of pure 1-(2',6'-dimethylphenylamino)-2-(4'-chlorophenyl-amino)-propane hydrochloride are obtained; m.p.: 170°-176° C. This salt is converted to the free base as described in Example 3, Method (b), point (b), and the base is separated by extracting the reaction mixture with chloroform.

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