Synthetic Communications p. 2101 - 2115 (2004)
Update date:2022-08-05
Topics:
Navratilova, Hana
Kriz, Zdenek
Potacek, Milan
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.
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