Globey - 3-8-2009 at 10:05
Literature on this is scarce, but could one simply reflux tramadol FB or HCL with conc. HBR, extract, and then a simple reduction? The HBR not only
strips the methyl (ether to alcohol), but dehydrates elsewhere to an alkene. Would simple activated Al in isopropanol be able to saturate the double
bond here? Or how about even simpler, use basic (NaOH) isopropanol/water and regular aluminum foil to go from the O-desmethyltramadene (faxeladene),
to the faxeladol, fb.
Tramadol & faxeladol are both unscheduled by US & UN AFAIK.
donlaszlow - 3-8-2009 at 12:03
Al might be a bit too harsh. Try hydrogenation with Pd, you need to be gentle.
This article is free to download, just google it:
Cuauhtémoc Alvarado, Ángel Guzmán, Eduardo Díaz, and Rocío Patiño, Synthesis of Tramadol and Analogous, J. Mex. Chem. Soc. 2005, 49(4), 324-327
They somewhat did the same thing
JohnWW - 3-8-2009 at 13:36
Those drugs, BTW, are analgesics, with opioid properties similar to morphine, but supposedly less addictive and less bitter-tasting. They have been
used in various countries including New Zealand, but their use is beset with a whole raft of unwanted side-effects. Look them up on Google and
particularly Wikipedia for further details.
Like true opioids (including synthetic ones like methadone and mepiridine and dextromethorphan), they conform structurally to the "morphine rule",
i.e. an aromatic ring, attached to a quaternary carbon, this attached to two (or sometimes more) carbons, and this attached to a tertiary amine
nitrogen. (This differs from amphetamine and its homologs, which are phenethylamines).