A. N-Formyl-α,α-dimethyl-β-phenethylamine. To a 2-l., three-necked, round-bottomed flask fitted with a sealed stirrer carrying a crescent-shaped blade, a thermometer, an addition funnel, and a reflux condenser connected to a trap containing 20% sodium hydroxide solution is added 500 ml. of glacial acetic acid (Note 1). The contents of the flask are cooled to 20° by means of an ice bath, the addition funnel is temporarily replaced by a stopper, and to the stirred acetic acid is added 110 g. (2 moles) of 95% sodium cyanide in small portions. The temperature of the mixture is maintained around 20°, and the addition requires about 20 minutes (Note 2). The addition funnel is replaced, and a previously prepared and cooled solution of 500 g. (272 ml., 4.9 moles) of concentrated sulfuric acid in 250 ml. of glacial acetic acid is added slowly, with stirring, the temperature of the mixture being kept at about 20° by means of an ice bath (Note 3). The ice bath is removed, and 300 g. (2 moles) of α,α-dimethyl-β-phenethyl alcohol (Note 4) is added over a 20-minute period during which the temperature of the mixture rises slowly to 35–45°. The reaction mixture is stirred for an additional 90 minutes (Note 5) and allowed to stand overnight. The amber-colored mixture containing some solid sodium sulfate is aerated with nitrogen for 2 hours (Caution! In a hood), poured into 3 l. of ice water, and the supernatant oil separated. The aqueous phase is neutralized with sodium carbonate and extracted with 600 ml. of ether. The ethereal extract is combined with the original oily supernatant, neutralized with sodium carbonate, and dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure, and the residue is distilled to yield 230–248 g. (65–70%) of product, b.p. 137–141° (2 mm.). Redistillation of the ether-containing fore-run yields up to an additional 14 g. of material.

B. α,α-Dimethyl-β-phenethylamine. In a 3-l., three-necked, round-bottomed flask equipped with a reflux condenser and a sealed stirrer are placed 246 g. (1.39 moles) of N-formyl-α,α-dimethyl-β-phenethylamine and 2.1 l. of 20% sodium hydroxide solution. The mixture is heated under reflux with vigorous stirring for 2.5 hours or until a test portion of the oily layer dissolves completely in cold 5% hydrochloric acid. The reaction mixture is cooled, 750 ml. of benzene is added, the mixture is stirred, and the benzene layer is separated. The benzene solution is shaken with a saturated sodium chloride solution, the benzene removed by distillation at atmospheric pressure, and the product distilled at reduced pressure to yield 155–165 g. (75–80%) of α,α-dimethyl-β-phenethylamine, b.p. 80–82° (10 mm.).