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tempidone fentanyl

Started by albert_grieves, January 26, 2004, 08:01:00 PM

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albert_grieves

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(GC_MS: "simple", General Discourse)
:
it is mentioned that 2,2,6,6 tetramethylpiperidone was bulky and could have some steric hindrance. does this mean 1. low yield 2. no yield 3. pharmacologically uninteresting fentanyl analog
my main questions are:
if you reacted p-methoxyphenyl-2-bromopropane with tempidone hcl ala seigfried would you get 1-(paramethoxyphenyl-2-propyl) 2,2,6,6 tetrametoxy-4-piperidone in at least 10% yeild?  whould reductive amination with aniline and acylation with acetic anhydride yield an opioid type compound? who cares to guess.  thanks in advance.

Rhodium

#3 is probably the biggest obstacle. I could only find one fentanyl analog reported in the literature with methyl groups in the 2/6 positions of the piperidine ring, and that was only one methyl group. No fentanyls with 2, 3 or 4 methyl groups in the 2/6 positions could be found. The 2-methylfentanyl was reported in

Patent US3923992




albert_grieves

thanks.  that kind of information is hard to find.  Looks like its back to methyl acrylate or the double mannich.  My dream compound would be a non-controlled fentanyl analog that is active in the 1-5mg range.  I was looking at loperamide molecules on google and I was amazed at the difference between that and fentanyl, and even loperamide is active with the microgranules.  I think there is a lot of room for finding an active compound that is not specifically listed.  I could mix it with sugar and tell the cops I was making my own rat poison.

Nicodem

if you reacted p-methoxyphenyl-2-bromopropane with tempidone hcl ala seigfried would you get 1-(paramethoxyphenyl-2-propyl) 2,2,6,6 tetrametoxy-4-piperidone in at least 10% yeild?

I'm sure that you would get a considerably higher yield reacting 1-(p-methoxyphenyl)-2-amino-propane (aka PMA) with phorone. The steric hinderance would not be so much of an obstacle as whith the N-alkylation reaction.