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Author Topic: Idea for phenmetrazine synthesis  (Read 326 times)

Balkan Bonehead

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Idea for phenmetrazine synthesis
« on: February 12, 2012, 07:56:49 AM »
So, the other day, I picked up a bottle of what claimed to be some kind of floor and tile stripper and inspected the ingredients; it said on the label: "contains monoethanolamine". Curious, I googled the term and discovered that a wide variety of cleaners, strippers, etc, contain monoethanolamine as the principle ingredient, some in quite concentrated form.

Now, monoethanolamine, if used to aminate either phenylacetylcarbinol or 1-phenyl-1,2-propanedione will yield a product that is only one step away from phenmetrazine, requiring only an acid-catalyzed ring closure. The 1,2 dione in particular is pretty easily made by acid hydrolysis of isonitrosopropiophenone, which itself is made by the action of nitrous acid on propiophenone.

Erowid says that 1-phenyl-1,2-propanedione will preferentially aminate on the 2 position, and the other ketone will be reduced to the alcohol, ie: http://www.erowid.org/archive/rhodium/chemistry/ephedrine.resolution.html. The only difference in this case is that we would be employing ethanolamine instead of methylamine. The big question is whether an Al/Hg reduction will be sufficient to reduce the aromatic ketone to an alcohol while simultaneously aminating the second ketone. I say yes, but that is just an educated guess.

Goldmember

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Re: Idea for phenmetrazine synthesis
« Reply #1 on: February 12, 2012, 09:20:56 AM »
Al/Hg is said to work in fair yield when methylamine is used, so I dont see why not.

jon

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Re: Idea for phenmetrazine synthesis
« Reply #2 on: May 20, 2012, 10:15:49 PM »
you can also oxidize propiophenone with mno2 and get the diketone

Sydenhams chorea

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Re: Idea for phenmetrazine synthesis
« Reply #3 on: May 23, 2012, 04:28:03 PM »
Quote from: jon on May 20, 2012, 10:15:49 PM
you can also oxidize propiophenone with mno2 and get the diketone

can you provide a ref for that?
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carl_nnabis

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Re: Idea for phenmetrazine synthesis
« Reply #4 on: June 01, 2012, 10:29:19 AM »
I am a bit curious about this: Wouldnt it be possible to reduce phenyl-2-nitropropanol (we call it P2NP-ol short) via nef reaction to racemic phenylacetylcarbinol? Essentially the same reaction to reduce P2NP to P2P, except that the nitroalcohol is saturated where P2NP is not, but P2P is, and PAC too.
Just curious because the double bond is on the same carbon where the keto-group will be after reduction and a friend said a few minutes ago that it doesnt matter if saturated or not.
That would be some good starting material for n-hydroxyethyl-ephedrin, i am really a lot interested in that stuff, it has an even higher dopamine to noradrenaline ratio(ergo more pleasure) than has methamphetamine! That should be some pretty nice addictive stuff to play around with ;D
« Last Edit: June 01, 2012, 10:36:04 AM by carl_nnabis »
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carl_nnabis

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Re: Idea for phenmetrazine synthesis
« Reply #5 on: June 04, 2012, 03:45:57 PM »
It will work as stated by few other people (who are talking out of their asses...), but were just speculating as no one could find a good reference easily, and i am not sure if it does work so i would just prove it in experiment, using stannous metal powder, or iron powder.
As agents for nitrogroups to carboxylic groups with reducing properties they would be that one of choice, because there are also a lot of references where a oxidating one is in use, but that would be unpreferable as there is a good chance that the alcohol will also be oxidized to the diketone and that would be the less preferred starting material.
Sn or Fe reduction is also documented to give a very good nearly to quantitative yield reducing nitrostyrene to their ketone counterpart. Both people I have asked said the double bond will not interfere in this reaction, but isnt that the essential part where reaction takes place? I am not sure if Fe or Sn is able to reduce double-bonds, but i doubt they will, so where is that unsaturated carbon-carbon bound then in the product?
Obviously this bound is then in use for the ketone group, correct me if i am wrong?

About the use of ethanolamine instead methylamine in a reductive amination, this is really exchangeable with nearly any common amine, or even nitroalkane in a al/hg reduction, when there is no steric hinderance to prevent this , but this is unlikely to happen with aliphatic primary amines like ethanolamine, they are not bulky enough.
« Last Edit: June 04, 2012, 03:50:23 PM by carl_nnabis »
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carl_nnabis

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Re: Idea for phenmetrazine synthesis
« Reply #6 on: July 13, 2012, 11:02:05 AM »
hey i got another idea, maybe forming the o-tosylate of norephedrine, then swap if possible '(should, because ring closure works the same in the original procedure using a bit tosylic acid) with 1,2 ethandiol (ethylene glycol) then again the tosylate in action for ring closure?  am i wrong?
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atara

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Re: Idea for phenmetrazine synthesis
« Reply #7 on: July 13, 2012, 06:58:08 PM »
Quote
Wouldnt it be possible to reduce phenyl-2-nitropropanol (we call it P2NP-ol short) via nef reaction to racemic phenylacetylcarbinol?

In principle yes but the reason you rarely see people talk about vicinal nitroalcohols is that they eliminate quite easily, and can undergo retronitroaldol reactions (esp. in basic conditions) more easily than their nitroalkene counterparts. The ordinary conditions of the Nef reaction might, therefore, generate a lot of side reactions.

The retronitroaldol of nitromyristicin is discussed in PiHKAL and similar reactions have been considered as a safe OTC route to nitroethane.

Assyl Fartrate

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Re: Idea for phenmetrazine synthesis
« Reply #8 on: September 15, 2012, 08:23:43 PM »
Calcium ethanolamine phosphate is sold as a dietary supplement.
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jon

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Re: Idea for phenmetrazine synthesis
« Reply #9 on: September 15, 2012, 11:14:54 PM »
"can you provide a ref for that?"

no but i know it's possible i've seen it in literature, take a notebook down to the library with these ideas and search the chem abs it's very lonely at the chemistry floor and chatty down at the law library.
fucking lawyers.
or do a google search

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« Last Edit: September 15, 2012, 11:42:42 PM by jon »
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