dormouse (Member)
04-23-00 04:38
No 108742
      Proposed Sesamol Analogue of MDMA Synth. -Aromaticity  Bookmark   


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Author  Topic:   Proposed Sesamol Analogue of MDMA Synth. 
Aromaticity
unregistered   posted 06-28-99 09:51 AM           
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Sesamol, I believe, is a natural oil best described as 1-hydroxy-3,4-methylenedioxybenzene.
One could therefore theoretically gently reflux sesamol in acetic anhydride using low heat with anhydrous conditions to obtain a compound exactly similar to MDP2P but with MDP2P's benzylic methylene unit replaced with an etheric oxygen. Of course, one should bee careful around ethers, as they can for explosive epoxides upon prolonged exposure to air.

Next, one could take this novel precursor compound and perform a gentle (i.e., ether approved) reductive amination with MeNH2 and your favorite reducing agent (such as NaBH4 perhaps) to yield 1-(3,4-methylenedioxybenzene)-OCH(CH3)NHCH3. Also,
NH2 could substitute for mehtylamine. Also, ethylamine could substitue for methylamine.

This is all just a thought at this point; however, with some more work and research, it could produce some active analogues, I think.


Beagle
Member   posted 06-28-99 09:20 PM          
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An interesting idea for an analog, since it should be nearly isosteric w/ MDA. The only similar cpd. I can think of is the phenoxy analog of TMA, which is apparently w/o activity. Of course TMA and MDA are quite different critters, so this doesn't really mean that much.
But I think that the method of prep. you suggest wouldn't work, being more likely to result in cleavage of the ester to the amide. Maybe a Leukardt reaction?

BTW, as you might have noticed, I always spell it "analog", which I thought was equally correct. But now I'm wondering if "analogue" is more correct, or prefered. Anyone have an OED handy?


Osmium
Member   posted 06-29-99 02:59 AM          
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You can't aminate esters. Doesn't work.
 
Aromaticity
unregistered   posted 06-29-99 08:16 AM           
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Beagle, "analogue" is the British spelling, but is used in American journals a lot, too. Analog is sometimes used as well, especially in America I think.
Osmium, you're right. The acetal intermediate is not going to endure those reducing conditions, is it? However, 1-amino-1-chloroethane might be a better alternative, when reacted with sesamol. I think I'll do some reasearch into this question. I sure it's not like this compound can't be synthesized somehow.


Labrat
Member   posted 06-29-99 09:55 AM          
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You could try starting with the 1-chloroethyl-phenyl ether and react this under PTC conditions with azide, as in Synth. Comm. 22: 2343 ('92). Reduce the azide to the amine with Mg or Ca like in TS. Lr/


Aromaticity
unregistered   posted 06-29-99 01:21 PM           
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Labrat,
Correct me if I'm wrong, but the procedure you described isn't going to make a compound containing a benzodioxole (i.e., a methylenedioxybenzene) ring system.
 
Beagle
Member   posted 06-29-99 03:03 PM          
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LR was refering to using the 3,4-MDphenyl ether.
On further reflection of this cpd., I'd say its a dud, since it is an aminal (amine analog of a acetal), it should be fairly rapidly hydrolyzed and inactivated.


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