METHOD OF SYNTHESIS OF 4-(4'-FLUOROPHENYL)-3-HYDROXYMETHYL-PIPERIDINES AND METHOD OF SYNTHESIS OF 4-(4'-FLUOROPHENYL)-3-(3',4'-METHYLENEDIHYDROXYPHENOXYMETHYL)-PIPERIDINE Russian patent published in 1999 - IPC

Abstract RU 2141477 C1

FIELD: organic chemistry, chemical technology. SUBSTANCE: invention relates to the improved method of synthesis of 4-(4'-fluoro-phenyl)-3-hydroxymethylpiperidines of the formula (I) where R₃ means hydrogen atom, C₁-C₆-alkyl or C₁-C₆-alkylaryl by reduction of the corresponding piperidine-2,6-dione of the formula (II) where R₃ has a value indicated above; R₄ is C₁-C₆-alkyl. Reaction is carried out in the presence of reducing agent - diborane in medium of an inert solvent, for example, tetrahydrofuran or dimethoxyethane. Invention also relates to the improved method of synthesis 4-(4'-fluorophenyl)-3-(3',4'-methylenedihydroxyphenoxymethyl)-piperidine of the formula (IIIa) by interaction of the compound of the formula (I) obtained by reduction of the compound of the formula (II) in the presence of diborane with benzosulfonyl chloride in the presence of N,N-dimethyl- -ethylamine and then in situ with sesamol. Obtained compound is subjected for interaction with phenylchloroformate and then with potassium hydroxide in toluene. The process of synthesis of the compound (IIIa) is simplified significantly by using diborane as a reducing agent at the first stage. EFFECT: improved and simplified method, increased yield of the end compound. 13 cl, 3 ex

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RU 2 141 477 C1

Authors

Sidnej Ehdvard Kehllender

Dates

1999-11-20—Published

1994-03-08—Filed