Ethylenediamine → Amantadine

Participants

Reaction Steps

Cleavage of 1-adamantanamine p-toluenesulfonamide. 1-Adamantanamine p-toluenesulfonamide (4 g, 0.13 mmol), n-propylamine (50 mL), and ethylenediamine (6.3 g, 0.11 mol) were placed in a 3 neck round bottomed flask equipped with a mechanical stirrer, condenser and thermometer. Lithium wire (0.64 g, 0.091 gram-atom) was added in two portions. Addition of one half of the lithium gave a dark color and the temperature rose to 42°. After an hour the temperature began to fall and the remainder of the lithium was added. The blue color dissipated over 45 min and the reaction mixture was poured onto ice and the resulting mixture was exacted with ether (3×50 mL). The ether was washed with brine and distilled at atmospheric pressure. The residue was sublimed at 90° (12 mm) to give 1.79 (91%) of 1-adamantanamine.

Provenance & Evidence