- Production Method of Pentacaine hydrochloride
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Pentacaine hydrochloride (CAS NO.: 77656-21-4), with its systematic name of Carbamic acid, (3-(pentyloxy)phenyl)-, 2-(1-pyrrolidinyl)cyclohexyl ester, monohydrochloride,trans-(+-)-, could be produced through many synthetic methods.
Following is one of the synthesis routes: By refluxing a solution of equimolecular quantities of 3-pentyloxyphenyl isocyanate (I) and trans-2-(1-pyrrolidinyl)cyclohexanol (II) in toluene. The obtained pentacaine base is transformed to the hydrochloride by treatment of an ether solution of anhydrous hydrogen chloride (1,2). The starting amino-alcohol (II) is prepared from cyclohexanol (III), which is first dehydrated to cyclohexene (IV). The following addition of HClO gives trans-2-chlorocyclohexanol (V), which, in turn is dehydrochlorinated to 1,2-epoxycyclohexane (VI). Final addition of pyrrolidine (A) yields the required intermediate (II).
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