3-(Methoxymethyl)-4-methylaniline → N-(1-ethylpropyl)-3-(methoxymethyl)-p-toluidine

A mixture of 3-(methoxymethyl)-p-toluidine (9.3 g), 5 angstrom molecular sieves (19 g) and diethyl ketone (40 ml) is stirred at room temperature for 15 hours. The mixture is then filtered. Additional diethyl ketone (10-15 ml) and molecular sieves (10 g) are added to the filtrate. After 40 minutes at 40° to 50° C., the reaction mixture is filtered and then concentrated under vacuum. The crude product (9.0 g) is dissolved in methanol (50 ml) and cooled to 10° C. Sodium borohydrate (3.7 g) and methanol (25 ml) are simultaneously added in small portions. Thirty minutes after these additions, the mixture is acidified with 10% hydrochloric acid while in an ice bath. The mixture is extracted with ether and the ether extract is discarded. The aqueous extract is made alkaline and then extracted with ether. The ether extract is dried over magnesium sulfate and concentrated to yield 8.1 g of an orange oil which is more than 97% homogeneous as estimated by gas-liquid chromatography. Fractional distillation yields a product having a boiling point of 120° to 125° C. at 0.4 to 0.5 mm pressure.