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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