Acetamide, 2-[2-(dimethylamino)ethoxy]-N-tricyclo[3.3.1.13,7]dec-1-yl-, hydrochloride (1:1)

Tromantadine Hydrochloride is a hydrochloride salt form of tromantadine, a cyclic amine with activity against herpes simplex virus. Tromantadine inhibits absorption of virions to cell surfaces, as well as penetration and uncoating of the virus.

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.

Molecular Weight:316.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:6
Exact Mass:316.1917559
Monoisotopic Mass:316.1917559
Topological Polar Surface Area:41.6
Heavy Atom Count:21
Complexity:326
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes