53783-83-8

Viru-Merz,Merz,W. Germany,1973

Tromantadine hydrochloride is used as antiviral agent effective against herpes simplex infections.

ChEBI: Tromantadine is a secondary carboxamide.

Adamantane is first reacted with chloroacetyl chloride to give chloroacetylaminoadamantane. 2.3 g Na (0.1 g-atom) were dissolved in 75 ml dimethylamino-ethanol. Then the excess alcohol was distilled off completely and the sodium salt developed was dried in a vacuum. After drying, the salt was dissolved in about 200 ml xylene. To thissolution.22.8 g (0.1 mol) chloroacetylaminoadamantane were added, heated for 10 hours under reflux in a 250-ml round-bottomed flask with a reflux cooler, and the sodium chloride developed subsequently filtered off.
Next the xylene was distilled away, the liquid residue dissolved in about 80 ml carbon tetrachloride and the hydrochloride precipitated through introduction of hydrochloric acid gas. The hydrochloride was dissolved in about 100 ml acetone and the solvent subsequently distilled away, whereby excess hydrochloric acid passed over with it. This operation was repeated until no excess acid was present.
A large excess of petroleum ether was added in a 500 ml three-necked flask provided with a stirrer and reflux cooler, to a concentrated acetonic solution of the hydrochloride and stirred for at least 1 hour, whereby the desired substance was deposited in a crystalline form. Finally, the substance was filtered away and dried in a desiccator. 14 g of the substance (15% of theory) were obtained.

Antiviral