Hexocyclium Methyl Sulfate

Hormonchemie Merck Clevenot Farmalabor Pol fa Biosedra Byk Gulden 

Methyl acrylate and N,N -dimethylethylenediamine are first reacted and that product reduced with lithium aluminum hydride to give a compound A. 

To a solution of 13 parts of compound A and 12 parts by volume of absolute pyridine in 80 parts by volume of absolute dioxane there are added dropwise and under constant stirring 35 parts of 3,4.5-trimethoxybenzoyl chloride dissolved in 70 parts by volume of absolute dioxane in the course of 30 minutes. The mixture is stirred for a further 3 hours at a temperature of 100°C and the excess solvent is then evaporated in vacuo. The residue of the evaporation is treated with ethyl acetate and saturated sodium carbonate solution, whereafter the organic phase is separated, treated with water, dried with sodium sulfate and the solvent is removed in vacuo. The residue thus obtained is taken up In ether and separated from 4 parts of insoluble trimethoxybenzoic acid anhydride by filtration. After evaporation of the ether there are obtained 32.5 parts of N,N -dimethyl-N,N -bis-[3-(3,4,5-trlmethoxybenzoxy)-propyl] -athylene diamine, corresponding to a yield of 86% of the theoretical. MP 75°C to 77°C. 

The di-tertiary base thus obtained is dissolved in ether and the solution Is saturated with hydrogen chloride gas. After isolation and reprecipitation from methanol-ether there Is obtained the dihydrochloride melting at 170°Cto 174°C. 

Kraupp, O. and SchlogI, K. U.S. Patent 3,267,103 August 16, 1966 assigned to Oesterreich-Ische Stickstoffwerke AG (Austria) 

Hormonehemie Merck Clevenot Farmalabor Polfa Biosedra Byk Gulden 

Trade Name Manufacturer Country Year Introduced 

Hormonchemie Merck Clevenot Farmalabor Polfa Siosedra 8yk Gulden 

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Hexamethonium bromide Hexocyclium methyl sulfate Ipronidazole Mefruside... 

Other drugs in this category include anisotropine methylbromide (Valpin), clidinium bromide (Quarzan also in combination with chlordiazepoxide as Librax and others), glycopyrrolate (Robinul also used parenterally in conjunction with anesthetics), isopropamide iodide (Darbid), mepenzolate bromide (Cantil), tridihexethyl chloride (Pathilon), and hexocyclium methyl-sulfate (Tral). 

Hexocyclium Methyl Sulfate. 4-(2-Cyclohexyt-2-hydroxy-2.phenylethyl)-l, l Hmethylpiperazi ium methyl sulfate (salt) N-(0-cyclohexyl -hydroxy-(3-phenylethyl)-AT -methylpiperazine methosulfate N-fp-cyclohexyl-(J-hydroxy-(J.phenylethyD-N -methylpiperazine dimethylsul -fate 4 -(0 -cyclohexyl -p -hydroxy -0 -phenethyl) -1,1 -dimeth -ylpiperazinium methyl sulfate Tral Tralin. mol wt 428.59. C 58.85%, H 8.47%. N 6.53%, O 18.67%, S 7.48%. Description Helgren ei of.. J. Am. Pkartn. Assoc-. Set Ed. 46, 639 (1957). Prepn Weston, U.S. pat. 2,907,765 (1959 to Abbott). 

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