Bisolvon,Boehringer Ingelheim,Switz.,1963
ChEBI: A substituted aniline that is 2,4-dibromoaniline which is substituted at position 6 by a [cyclohexyl(methyl)amino]methyl group. It is used (as the monohydrochloride salt) as a mucolytic for the treatment of respiratory disorders associated with productive
ough (i.e. a cough characterised by the production of sputum).
In initial steps, 2-nitrobenzylbromide and cyclohexylmethylamine are reacted
and that initial product reacted with hydrazine to give N-(2-aminobenzyl)-Nmethyl-
cyclohexylamine.
A solution of 29.3 g of bromine in 50 cc of glacial acetic acid was slowly added
dropwise to a solution of 159 g of N-(2-aminobenzyl)-N-methylcyclohexylamine,
accompanied by stirring. The glacial acetic acid was
decanted from the precipitate formed during the addition of the bromine
solution, and the precipitate was thereafter shaken with 200 cc of 2N sodium
hydroxide and 600cc of chloroform until all of the solids went into solution.
The chloroform phase was allowed to separate from the aqueous phase. The
chloroform phase was decanted, evaporated to dryness and the residue was
dissolved in absolute ether. The resulting solution was found to be a solution
of N-(2-amino-3,5-dibromobenzyl)-N-methyl-cyclohexylamine in ethanol. Upon
introducing hydrogen chloride into this solution, the hydrochloride of N-(2-
amino-3,5-dibromobenzyl)-N-methyl-cyclohexylamine precipitated out. It had
a melting point of 232°-235°C (decomposition).
