Pirmenol hydrochloride, CI-845, Pimenol, Pimavar

吡美诺 Chemical Name: (?-cis-2,6-Dimethyl-alpha-phenyl-alpha-(2-pyridyl)-1-piperidinebutanol monohydrochloride; (?-1-Phenyl-1-(2-pyridyl)-4-(cis-2,6-dimethyl-1-piperidyl)butanol monohydrochloride; (?-cis-alpha-[3-(2,6-Dimethyl-1-piperidinyl)propyl]-alpha-phenyl-2-pyridinemethanol monohydrochloride
CAS No. 61477-94-9, 68252-19-7 (free base)
项目整合开发状态: Launched-1994
项目研究机构: Pfizer (Originator), Dainippon Pharmaceutical (Licensee)
合成路线:The reaction of gamma-chlorobutyrophenone (I) with ethylene glycol (II) by means of p-toluenesulfonic acid in refluxing benzene gives the corresponding ethylene ketal (III),which is condensed with cis-2,6-dimethylpiperidine (IV) by means of Na and heat,and hydrolyzed with concentrated HCl yielding gamma-(cis-2,6-dimethyl-1-piperidyl)butyrophenone (V).Finally,this compound is condensed with 2-bromopyridine (VI) by means of butyllithium in THF.

合成路线:The reaction of dimethylpiperidine (IV) with 3-bromopropanol (VII) in refluxing xylene gives 1-(3-hydroxypropyl)-2,6-cis-dimethylpiperidine (VIII),which by treatment with SOCl2 in refluxing benzene is converted into 1-(3-chloropropyl)-2,6-cis-dimethylpiperidine (IX).Finally,this compound is condensed with 2-benzoylpyridine (X) by means of Li in THF.