- Production of Tiquizium bromide
Tiquizium bromide (CAS NO.: 71731-58-3), with its systematic name of trans-3-(Di-2-thienylmethylene)octahydro-5-methyl-2H-quinolizinium bromide, could be produced through many synthetic methods.
Following is one of the synthesis routes:
Firstly, 2-piperidineethanol (I) could react with acrylonitrile (II) to produce N-(2-cyanoethyl)piperidine-2-ethanol (III), which by treatment with SOCl2 is converted into the chloronitrile (IV). Next, the cyclization of (IV) with NaH affords 3-cyanoquinolizidine (V), which by hydrolysis with ethanol and HCl yields ethyl quinolizidine-3-carboxylate (VI). The Grignard reaction of (VI) with 2-thienylmagnesium bromide gives thienyl-3-quinolizidinyl methanol (VIII), which is dehydrated with HCl ethanol to afford 3-(di-2-thienylmethylene)quinolizidine (IX). At last, this compound is quaternirzed with methyl bromide in acetone.
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