chemrox - 31-7-2007 at 21:38
I found a syn of 1-methyl-1,2,3,4-tetrahydropyridine starting from 1-methyl-1,2,3,6-tetrahydropyridine.. a matter of moving the double bond (J, Org.
Chem. 1980,45, 1336-1338). The products are in equlibrium so the yield isn't great I'm wanting to make the 1,2,3,4 isomer and haven't found it
elsewhere yet in the literature but that may just be a library trip to get to the abstracts and Beilsteins. I undrstand this could be made through
the pyridinium salt. So how does one get to the 1-methyl pyridinium? [What is it called?]Wouldn't a carbanion, say from MeI do the job? A Hoffmann
degradation? is there a catalyst like Ag2O required?
[Edited on 31-7-2007 by chemrox]
jon - 2-8-2007 at 18:35
yes this is a quaternary ammonium salt so reaction of pyridine with any alkyl halide would produce it's quaternary salt.
AgO is what you use to reduce quaternary salts back to tertiary amines.
chemrox - 3-8-2007 at 00:50
OIC-thanks