hexocyclium metilsulfate

hexocyclium metilsulfate Chemische Eigenschaften,Einsatz,Produktion Methoden

• Originator

  Tral,Abbott,US,1957

• Verwenden

  Hexocyclium inhibits muscarinic action of acetylcholine on postganglionic parasympathetic effector regions. It is used for treating stomach ulcers.

• Definition

  ChEBI: Hexocyclium methyl sulfate is a member of phenylethanolamines, an ethanolamine sulfate salt and a piperazinium salt.

• Manufacturing Process

  In a 2-liter, 3-necked, round-bottomed flask equipped with a stirrer, dropping funnel, and a condenser protected with a calcium chloride drying tube is placed 13.7 grams (0.57 mol) of magnesium turnings and the magnesium is covered with 200 cc of anhydrous ether. A crystal of iodine is added to the flask and 92.9 grams (0.57 mol) of cyclohexyl bromide dissolved in 300 cc of anhydrous ether is added dropwise with stirring while the reaction proceeds. After the addition of the cyclohexyl bromide is completed, the resulting mixture is stirred and heated on a steam bath for 3 hours. The mixture is cooled to room temperature and 49.5 grams (0.227 mol) of N-phenacyl-N'- methylpiperazine dissolved in 50 cc of anhydrous ether is added dropwise and the resulting mixture is stirred and re fluxed for about 16 hours.
  The reaction mixture is cooled and 50 grams of ammonium chloride dissolved in 200 cc of water is added dropwise thereto with stirring. The decomposed Grignard complex is then filtered. Benzene is added to the ether filtrate and the solvents are removed therefrom on a steam bath. The residue is fractionated and the base, N-(β-cyclohexyl-β-hydroxy-β-phenyl-ethyl)N'- methylpiperazine, is obtained as a liquid having a boiling point of 196° to 203°C at a pressure of 4.0 mm.
  To 3.8 grams of the base dissolved in 35 cc of ethyl alcohol is added 1.6 grams of dimethyl sulfate. The solution is allowed to stand at room temperature for about 12 hours. The salt formed is filtered, recrystallized from ethyl alcohol, and is found to have a melting point of 203° to 204°C.

• Therapeutic Function

  Spasmolytic

• Synthese

  Hexocyclium, 4-(|?-cyclohexyl-|?-hydroxyphenethyl)-1,1-piperazinium methylsulfate (14.1.28), is synthesized by alkylating 1-methylpiperazine with |á-bromacetophenone, which forms 4-methyl-1-phenacylpiperazine (14.1.26). Reacting this with cyclohexylmagnesiumbromide gives 4-(|?-cyclohexyl-|?-hydroxyphenethyl)-1,1-piperazine (14.1.27), the alkylation of which using dimethylsulfate gives hexocyclium [23].

  

hexocyclium metilsulfate Upstream-Materialien And Downstream Produkte

hexocyclium metilsulfate Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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