Author Topic: Bromo-DragonFLY & Phenmetrazine syntheses  (Read 560 times)

Naf1

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Re: Bromo-DragonFLY & Phenmetrazine syntheses
« Reply #20 on: February 25, 2010, 08:43:48 PM »
Regarding amine protection and why its there, the use of triflouroacetamide in the above synthesis is as was not for the bromination but for the subsequent aromatization with dichlorodicyanobenzoquinone which is a powerful oxidant. Which is all covered in this paper;

A Novel (Benzodifuranyl)aminoalkane with Extremely Potent Activity at the 5-HT2A Receptor1
Matthew A. Parker, Danuta Marona-Lewicka,
Virginia L. Lucaites,† David L. Nelson,† and
David E. Nichols*
J. Med. Chem. 1998, 41, 5148-5149
http://www.unc.edu/~dlinz/Papers/A%20Novel%20(Benzodifuranyl)aminoalkane.pdf

no1uno

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Re: Bromo-DragonFLY & Phenmetrazine syntheses
« Reply #21 on: February 26, 2010, 09:18:29 PM »
Yeah, they use the same TFA-protected amine to oxidize the ring to the aromatized variant - Shulgin uses something similar to make DOI remember? So the use of a protected amine - even with the Friedel-Crafts acylation (especially if we can expect racemization due to the workup being basic & Cathinones being noted for their virtually complete racemization in basic solution), we still have to see whether or not the oxazoline formed by Benzoic anhydride and the chloroamino acid would acylate the substrate.

I'm also looking into what would happen if we nitrated the substrate first, 2,5-dimethoxynitrobenzene... The nitro-group should force p-acylation, as should 2,5-dimethoxychlorobenzene (really)... That would move the yield limiting step to the front, while we are dealing only with hydroquinone derivatives and allow for much easier and quicker processing post acylation, as well as reducing the amount of amino acid that has to be played with (protection and chlorination aren't going to be trivial).

Shroomed...,

I think DOC shows better trip reports than even the 2C series
"...     "A little learning is a dang'rous thing;
    Drink deep, or taste not the Pierian spring:
    There shallow draughts intoxicate the brain,
    And drinking largely sobers us again.
..."

Naf1

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Re: Bromo-DragonFLY & Phenmetrazine syntheses
« Reply #22 on: February 26, 2010, 10:23:38 PM »
"they use the same TFA-protected amine to oxidize the ring to the aromatized variant - Shulgin uses something similar to make DOI remember?"

It is also referred to as dehydrogenation.

Dichloro Dicyano Quinone (DDQ)
http://www.simafex.com/_pdf/ddq.pdf


xman47

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Re: Bromo-DragonFLY & Phenmetrazine syntheses
« Reply #23 on: October 21, 2011, 09:22:03 PM »
Thanks to Naf1 for posting the phenmetrazine synthesis.

I have one question, could you please be more specific on the Pd/C conditions ?

Also, is it possible to make it from norephedrine ? I think the answer to this one is no, and also the norephedrine aquisition is problematic, but ... just in case, curious about it.


The 2C-B fly is a bit too much for me at this time.


I have made my own 2C-B, 2C-C and DOM though, and I am currently interested in the DOX's. I am looking into how to keep the good feeling of the DOX's while minimizing the bad trip like effects.

Currently I have tried DOM and DOC, I like both. Planning on DOET.

POSEIDON

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Re: Bromo-DragonFLY & Phenmetrazine syntheses
« Reply #24 on: October 21, 2011, 09:58:54 PM »
look this article
The chemists are a strange class of mortals, impelled by an almost insane impulse to seek their pleasures amid smoke and vapour, soot and flame, poisons and poverty; yet among all these evils I seem to live so sweetly that may I die if I were to change places with the Persian king.
— Johann Joachim