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Author: Subject: i wonder if i can brominate this?
jon
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[*] posted on 10-7-2012 at 12:46
i wonder if i can brominate this?


with just bromine in acetic acid.
see the alpha proton on the ester is resonanace stablized.
but the benzylic carbon is attached to deactivating ester and activating piperidine ring.
the compound is ethyl phenidate and on halogenation it becomes more addictive than cocaine.
and 4-7 times more powerful depending.
mice prefer it to cocaine.

here is an example:
http://en.wikipedia.org/wiki/3,4-Dichloromethylphenidate

the dichloro compound is usually made from the dichloroacetonitriles and 2-bromopyridine.
i suspect it is possible to skip this altogether looking at the degree of ring activation going on here.


also the rpaidity of onset can be solved by using the isopropyl or tert butyl esters as they are much more lipophillic and the subjective (rush) is there.


[Edited on 10-7-2012 by jon]

[Edited on 10-7-2012 by jon]

[Edited on 10-7-2012 by jon]




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SulfurApothecary
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[*] posted on 10-7-2012 at 20:07


I think you can brominate this, I looked at what it is and it seems plausible. But, please make your question more coherent so I might be able to help. (this is purely educational right?). Please rephrase your statements as questions.

Also, I know the legal status is, "unscheduled" but please be careful with addictive narcotics... Don't do anything illegal. As of now, science madness has not been taken over my drug manufacturing.




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jon
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[*] posted on 10-7-2012 at 21:37


no no i just want to test it on mice.
to be more lucid is that ring activated enough to brominate in GAA?
i want to see if i can get mice to chose over food or companionship.
if i can, well it works that way to for us which means emptied bank accounts ok ya got me!

[Edited on 11-7-2012 by jon]




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[*] posted on 11-7-2012 at 18:52


I would think it would work if you use a lewis acid catalyst for electrophilic substitution, such as FeBr3. Instead of taking the Dichloromethylphenidate and brominateing it, it would be much better to take Methylphenidate and brominate it with the above method (electrophilic substitution).







So the benzene ring will be brominated, and it can be made into Dibromomethylphenidate

Did that help? I don't think you can make it with GAA and pure bromine. To me, I would think that would be the only way to make it.

[Edited on 12-7-2012 by SulfurApothecary]




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[*] posted on 11-7-2012 at 23:27


no because if you throw catalyst in the mix the alpha hydrogen of the ester gets brominated to.
if it will work on toulene it will work in this case about the same degree of activation.
look at the groups tied to that benzylic carbon they balance one another out.
as far as ring activation goes.
one withdraws electron and the piperidine ring donates evens it out to where it just might work.

[Edited on 12-7-2012 by jon]




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12-7-2012 at 00:32

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