triclobisonium chloride

Originator

Triburon,Roche,US,1959

Manufacturing Process

To a solution of 49 grams (0.25 mol) of cis-tetrahydroionone and 14.1 grams (0.12 mol) of 1,6-hexanediamine in 150 ml of ethanol was added 1 teaspoon of Raney nickel. The volume was adjusted to 300 ml with ethanol and the mixture was hydrogenated at 50°C and a pressure of 200 psi. The catalyst was filtered off, the filtrate was concentrated and the residual oil fractionated in vacuo to obtain N,N'-bis[1-methyl-3-(2,2,6-trimethylcyclohexyl)propyl]-1,6- hexanediamine; BP 192° to 202°C at 0.02 mm.
To 217 grams (0.456 mol) of N,N'-bis[1-methyl-3-(2,2,6- trimethylcyclohexyl)propyl]-1,6-hexanediamine were added 182 ml (3.04 mols) of formic acid (90%). The resulting colorless solution was cooled, then 91.3 ml (1.043 mols) of formaldehyde (37%) were added. The solution was heated at steam temperature with occasional shaking for 2 hours and then refluxed for 8 hours. The volatiles were distilled off at steam temperature under water vacuum and the residual oil was made strongly alkaline with 50% potassium hydroxide. The reaction product was extracted with ether. The ether extract was washed with water, dried and concentrated in vacuo. The residual oil was fractionated in vacuo to obtain N,N'-bis[1-methyl-3-(2,2,6- trimethylcyclohexyl)propyl]-N,N'-dimethyl-1,6-hexanediamine, BP0.4 230° to 240°C, nD26 = 1.4833. An aliquot, when treated with an ethanolic hydrogen chloride, gave the crystalline dihydrochloride, MP 183° to 185°C (recrystallized from ethanol-acetonitrile).
To 5 grams of N,N'-bis[1-methyl-3-(2,2,6-trimethylcyclohexyl)propyl]-N,N'- dimethyl-1,6-hexanediamine dissolved in 100 ml of methanol, at 4°C. were added 100 ml methanol containing 10 grams of methyl chloride. The solution was heated in a closed vessel at 60°C for 15 hours. The colorless solution was concentrated and the resulting white solid crystallized from ethanol_x0002_acetonitrile-ether to obtain N,N'-bis[1-methyl-3-(2,2,6- trimethylcyclohexyl)propyl]-N,N'-dimethyl-1,6-hexanediamine bis(methochloride) hemihydrate.

Therapeutic Function

Antiseptic

Safety Profile

Poison by ingestion,subcutaneous, intravenous, and intraperitoneal routes.When heated to decomposition it emits toxic fumes of Clíand NOx.