A rubber tube from an inverted cylinder of liquid ammonia is attached to a glass tube which extends beneath the surface of 325 ml. of 90% ethanol in a 500-ml. Erlenmeyer flask. Ammonia is passed into the ethanol until the weight increases by 41 g. (2.4 moles). The flask is cooled in ice water occasionally in order to hasten the absorption of the ammonia.

The ethanolic ammonia is added to 49 g. (0.16 mole) of di-n-butylaminoethyl bromide hydrobromide [Org. Syntheses Coll. Vol. 2, 92 (1943)] (Note 1) in a 1-l. round-bottomed flask. The flask is stoppered tightly and allowed to stand for 6 days at room temperature. The solution is then transferred to an evaporating dish and stirred while it is evaporated to a crystalline paste under a hood. The crystalline paste is transferred to a 400-ml. beaker, and to it is added a solution of 16 g. of sodium hydroxide in 18 ml. of water. The solution separates into an upper layer of brown oil and a lower layer which contains a considerable amount of undissolved sodium bromide. About 10 ml. of water is added to dissolve most of the precipitate. The whole is then extracted with three 50-ml. portions of benzene. The combined extracts are placed in a 250-ml. flask over 15 g. of potassium carbonate and set aside to dry overnight.

The dried benzene extract is placed in a 250-ml. flask fitted with a 30-cm. fractionating column, and the benzene is removed by distillation at atmospheric pressure. Fractionation of the residue is carried out under reduced pressure using a 50-ml. Claisen flask with a built-in 12- to 15-cm. Vigreux column. The fraction boiling at 100–103°/13 mm. is collected; it weighs 11 to 14.7 g. (41–55%) (Note 2).