The Vespiary
The Hive => Chemistry Discourse => Topic started by: Chemikaze on December 22, 2002, 09:40:00 AM
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A theoretical interest.
There is a "cheap" analgetic (maybe not analgetic itself but used in analgetic pills,tempidone - [33973-59-0]) which is 2,2,6,6-tetramethyl-4-piperidone.
I wonder if it could give some unexplored(?) fentanyl analogue,if we substitute 4-piperidone in fent synth for this tempidone?
When I die bury me upside down so the world can kiss my ass.
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Yes, alkylating Tempinone(what country is this found in and whatis the active dose?) with phenethylchloride then following through with the standard fentanyl reactions (condensation w/ aniline, reduction of enamine and acylation of resulting anilide) willl indeed produce an active fentanyl congener. No refs on hand, but if you really want I'll dig them out. Searching USPTO will reveal info on this fenatnyl analogue.
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of the precursor 2,2,6,6-tetramethyl-4-piperidone is possible, IIRC, from ammonia and three moles acetone. 2,2,6,6-tetramethyl, that's pretty bulky, I guess some steric hindrance.
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Nemo_Tenetur, you 're right. A double aldol reaction on the acetone, followed by water elimination should give (CH3)2C=CH-CO-CH=C(CH3)2. Then a michael addition whith NH3 (followed by the same intramolecular reaction) should cyclizise the compound.
OK, this may be a little off-topic, but I know in literature there is described a mannich reaction between 3,5-(dicarboxymethyl)-4-heptanone, formaldehyde & methylamine to yield N-methyl-3,5-(diethyl)-3,5-(dicarboxymethyl)-4-piperidone (cfr. Chem. Ber. (1936) vol 69 p 2299). When this reaction is done with 2,4-(dicarboxymethyl)-3-pentanone, followed by decarboxylation, one obtains N-methyl-3,5-(dimethyl)-4-piperidone.
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No need to dig up those refs,Ritter,unless anyone else wants.
It is available in Russland,active dose is 25mg.
It is possible to acquire <2,5gr for $3.
P.S.Tried to find that patent but failed...
When I die bury me upside down so the world can kiss my ass.
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because I´m interested in piperidone chemistry. Some piperidinering-methylation seems to increase the potency of inversed pethidine-esters. I´ll look at the reference next week in the library if this is a clandestine useful synthesis (no pressure, precursors available & not too expensive).