Benzene → 2-[(7-Aminoheptyl)amino]ethan-1-ol

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Reaction Steps

The intermediate N-(2-hydroxyethyl)-1,7-heptanediamine was prepared in two steps as follows: To a stirred and ice-cooled solution containing 650 ml. of benzene and 43.5 g. of pyridine was added dropwise over a period of 30 minutes 75 g. of ethyl oxalyl chloride followed by dropwise addition over a period of 30 minutes 63 g. of 7-amino-heptanonitrile. The reaction mixture was stirred in the ice bath for 3 minutes, next stirred at room temperature for 45 minutes and then allowed to stand overnight at room temperature. The white solid was filtered off and rinsed with fresh benzene. The combined benzene filtrates were washed successively with two 250 ml. portions of 5% aqueous glycine solution containing 25 ml. of 10% aqueous potassium hydroxide solution, a 250 ml. portion of 0.6N hydrochloric acid and two 250 ml. portions of water. The benzene solution was then dried over anhydrous magnesium sulfate and evaporated in vacuo to yield 102.7 g. ethyl N-(6-cyanohexyl)oxamate. A 23.1 g. portion was fractionally distilled at high vacuum for analysis, thereby yielding 14.7 g. of ethyl N-(6-cyanohexyl)oxamate, b.p. 170°-174° C. at 0.05 mm.

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