N,N-DMT from tryptamine via Al/Hg

[raffike]

Since it's possible to methylate amphetamine with formaldehyde and then reduce imine with aluminium amalgam,why shouldn't it be possible to dimethylate tryptamine?It's all in theory but suppose somebody mixed 1 mole of tryptamine with 2 moles of aqueous formaldehyde,added a certain amount of solvent(MeOH,EtOH or IPA for example),added little excess of sheet aluminium and knives edge worth of HgCl2 and let it reflux til Al was gone,basified,extracted with NP and gassed.It might not so simple but should be possible.It is possible with borohydride.Just a thought...
EDIT:The gassing part is bullocks,i realized,but an a/b should work...

[pHarmacist]

For N methylation of tryptamines see the last step in

Post 405291

(pHarmacist: "Synth. of 5-halo-tryptamine derivatives", Tryptamine Chemistry)

[raffike]

I know it works perfectly with NaCNBH3 but i'm merely asking if it worked with Al/Hg also.If it doesn't,SWIM will rush down to local supplier and will buy some cyanoborohydride but Al/Hg seems to be viable route also,at least in theory...

[urushibara]

Could the Al/Hg reaction be used to aminate indole-3-acetaldehyde? This would require dimethylamine, but, could it be done? Or would Al/Hg bugger up the indole rings? Or is the alphamethyl part of why al/hg works with p2p and mdp2p?

I found something: indolecarboxaldehyde + ethylchloroacetate-->indole-3-acetaldehyde. Those two chemicals would seem to me like good ones for not being watched. this looks like a promising route to dmt, det etc.

sorry if I'm covering old ground again here, I utfse and only found one post mentioning indoleacetaldehyde...

I should look into this subject...

[hypo]

> the only thing is, how to get indole acetaldehyde.

hm, like this:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/indoleacetaldehyde.html

?

otoh this synthesis needs painfully lots of solvent.

> turn the carboxylic acid into the ketone

aldehyde. carboxylic acids give aldehydes.

> that double bonded oxygen will usually go in any reaction before the hydroxyl.

nah. but the aldehyde is usually further reduced to the alcohol.

[urushibara]

just found that after posting that one  

All my chem knowledge just fell out of my head. ketone: double bonded oxygen with carbons either side on the chain, aldehyde, with just a hydrogen on one side and a double bonded oxygen... ie ketone is not on a terminal carbon, aldehyde is... I know you know that. I forgot.

Wouldn't it be tryptophol then if IAA was fully reduced?

and I spotted this one on the tryptophol synthesis page:

N-disubstituted tryptamines are obtained in high yield on boiling a solution of tryptophols in benzene or xylene with secondary amines and a nickel catalyst.

nice

so how does this sound -

IAA --> tryptophol via Ni catalyst or other gentle reduction.

tryptophol + dimethylamine --> dmt via nickel catalyst

would that work? would it be best catalytic or high-pressure?

have I read this all wrong? It sounds too easy. I can't seem to find any info on IAA->tryptophol, but it seems reasonable.

It'd be nice for the factor of being able to use cheap ass urushibara, which is said to be quite a gentle reducing agent.