n-Heptylamine (CAS NO.: ), which is also known as heptylamine, could be produced through the following synthetic routes.

A solution of 258 g. (2 moles) of heptaldoxime (p. 313) in 4 l. of absolute alcohol is heated to boiling in a 12-l. round-bottomed flask on a steam bath. The flask is equipped with a 150-cm. reflux condenser in which the inner tube is very wide (2.5 cm.). As soon as the alcohol begins to boil, the steam is shut off and the temperature is maintained by introducing strips of sodium through the top of the condenser. The total amount of sodium added is 500 g., and it should be added as rapidly as is possible without loss of alcohol. The last 150 g. of sodium melts in the hot mixture and may be added very rapidly without loss of alcohol or amine.

As soon as the sodium has dissolved, the contents of the flask are cooled and diluted with 5 l. of water. The flask is equipped at once with a condenser set for distillation, and the distillate is carried below the surface of a solution of 300 cc. of concentrated hydrochloric acid in 300 cc. of water in a 12-l. flask. The distillation is continued as long as any basic material passes over. When frothing interferes toward the end of the distillation an additional 3 l. of water is added to the distillation flask. The total distillate is 8–9 l.

The alcohol, water, and unreacted oxime are removed by heating the acid distillate on the steam cone under reduced pressure (about 20–30 mm.); the amine hydrochloride crystallizes in the flask. The flask is then cooled and equipped with a reflux condenser through which 1 l. of 40 per cent potassium hydroxide solution is introduced. The hydrochloride is washed down from the sides of the flask, and the resulting mixture is cooled and transferred to a separatory funnel. The lower alkaline layer is removed and solid potassium hydroxide is added to the amine in the funnel. The aqueous layer is removed and fresh sticks of potassium hydroxide are added from time to time until no further separation of an aqueous alkaline solution occurs. Twenty-four to thirty hours is required for complete drying. The amine is then decanted through the top of the funnel into a 250-cc. modified Claisen flask and distilled. The n-heptylamine is collected at 152–157°. The yield is 140–170 g. (60–73 per cent of the theoretical amount).