ORG-22110(monohydrochloride), ORG-23366

Chemical Name: 4-[4-[Bis(4-fluorophenyl)methylene]piperidin-1-yl]-1-(1-pyrrolidinyl)-1-butanone; 1-[4-[4-[Bis(4-fluorophenyl)methylene]-1-piperidinyl]butyryl]pyrrolidine
CAS No. 187673-38-7, 187673-37-6 (monoHCl), 187673-40-1 (monomethanesufonate salt), 187673-39-8 (monooxalate salt)
项目整合开发状态: Preclinical
项目研究机构: Akzo Nobel (Originator)
合成路线:Ethyl isonipecotate (I) was protected as the N-trityl derivative (II) using triphenylmethyl chloride and triethylamine.Addition of Grignard reagent (IV) (prepared from 1-bromo-4-fluorobenzene (III) and magnesium in Et2O) to (II) produced the diaryl carbinol (V).Alcohol dehydration with simultaneous trityl group cleavage under acidic conditions yielded 4-[bis(4-fluorophenyl)methylene]piperidine (VI).4-Chlorobutyrylpyrrolidine (IX),prepared by coupling of 4-chlorobutyryl chloride (VII) and pyrrolidine (VIII),was then condensed with piperidine (VI) to yield the target compound.