Microwave-Assisted Elimination Reaction of trans-4-(4-Fluorophenyl)-3-chloromethyl-1-methylpiperidine on Alumina

trans-4-(4-Fluorophenyl)-3-chloromethyl-1-methylpiperidine 3b was subjected to elimination reaction on alumina or KF-alumina under solvent-free conditions and microwave irradiation. Compared with the "classical" method of heating in the presence of an organic base, the microwave-assisted m...

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Bibliographic Details
Published in:Synthetic communications 2004-12, Vol.34 (11), p.2101-2115
Main Authors: Navrátilová, Hana, Kříž, Zdeněk, Potáček, Milan
Format: Article
Language:English
Subjects:
Alumina
Dehydrohalogenation
Elimination reaction
Microwave irradiation
Paroxetine
Solid support
trans-4-(4-Fluorophenyl)-3-chloromethyl-1-methylpiperidine
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Summary:trans-4-(4-Fluorophenyl)-3-chloromethyl-1-methylpiperidine 3b was subjected to elimination reaction on alumina or KF-alumina under solvent-free conditions and microwave irradiation. Compared with the "classical" method of heating in the presence of an organic base, the microwave-assisted methodology provided higher yields of 4-(4-fluorophenyl)-3-methylene-1-methylpiperidine 7b (65.5-71%) in considerably shorter reaction times (20-40 min). Furthermore, the exocyclic double bond in 7b underwent rearrangement to the endocyclic double bond to furnish compound 8. The effect of alumina and irradiation time on reaction conversion and the extent of isomerization was examined.
ISSN:0039-7911
1532-2432
DOI:10.1081/SCC-120037925