jon
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Registered: 11-1-2006
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Mood: paranoid distrustful apprehensive
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aza prins reaction of (tris)3-phenylpropan-1-ol-n,n,n,1,3,5 hexahydrotriazine with benzene-1-methyl-1-ethenyl and propionic acid, is it feasible?
i don't have chemdraw
imagine this:
3-amino-1-phenylpropan-1-ol is condensed with formalin to yeild the aforementioned trimer.
this is reacted with alpha methylstyrene and propionic acid catalyzed by phosphoric acid and a little propionic anhydride to abstract any water.
the concievable product would be 4-phenyl-4-propionoxy-1-(3-phenyl-3-propionoxy)piperidine.
a diester analgesic compound.
related compounds distill at 230 degrees celcius.
my question this obviously having a higher molecular weight/boiling point.
what is the probablilty of ester pyrolysis to give alkene products.
i'll have to write a dissertation to explain it fully.
primary esters pyrolyze at temperatures of 570 C just to give you an idea.
would this fly?
p.s. attached is something related just to give you an idea.
the above ester would be about 3000 times stronger than demerol.
the second pdf is the reaction i'm talking about.
i poured a lot of research into the possible mechanism.
it's called aza-prins it's a variation of the prins reaction using amines.
here is a rundown of the prins reaction.
http://en.wikipedia.org/wiki/Prins_reaction
the absence of water results in esters.
the triazine splits into monomers, which undergo acid catalyzed amino methylation reaction with alpha-methylstyrene the double bond shifts and a
second sucessive aminomethylation takes place.
(i don't claim to have the entire mechanism understood.)
the final intermediate is a tertiary carbonium ion which gets attacked by the carboxylic acid to give rise to these reversed esters of demerol.
My question is simply this:
would these high boiling esters distill without pyrolysis to thier respective alkenes???
[Edited on 7-7-2011 by jon]
[Edited on 7-7-2011 by jon]
Attachment: 37746344-226-Derivatives-of-4-ethoxycarbonyl-and-4-hydroxy-4-phenyl-piperidine.pdf (981kB)
This file has been downloaded 502 times
[Edited on 8-7-2011 by jon]
Attachment: prodine.pdf (15kB)
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[Edited on 8-7-2011 by jon]
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jon
Hazard to Others
Posts: 459
Registered: 11-1-2006
Member Is Offline
Mood: paranoid distrustful apprehensive
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nevermind pyrolysis to alkenes under hard vacumm of tert esters occur at 600K or so.
between 300-330 C
not a hard and fast rule because it largly depends on substrate.
and it's electronic character.
in this case (benzylic esters) the pyrolysis is probably even more energetically favorable.
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