N,n-DET via reductive amination from tryptamine using acetaldehyde?

Rabidreject

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Okay I have been trying out this synthesis, iv failed once and I think I know what I did wrong but has anyone successfully done this? I actually have access To TLC now so should be able to see what’s going on a bit better and if it is actually reducing to one substance….

I don’t see how it could be that different to other cold reductive amination of tryptamine though….the stoichiometry all works out…well as far as I can see…I’m certainly no master - or barely even an amateur!

im taking notes on everything I do and I know my reagents are good so if it’s simply a case of no 1 has tried it coz they don’t want DET then I shall carry on trying but obviously if someone’s done this, point me in the right direction?

im not sure I kept it cold enough last time….
 

gnbarsh3463_11

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Yes, this can be done for sure.
 

Rabidreject

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Okay smashing…

im assuming I didn’t keep it cold enough last time and got a b-carboline side product or something instead.

This is a reaction I have been meaning to come back to actually…

I ran the reaction and have basically been both, working on another reaction in the meantime (a Henry/nitroaldol reaction on 2,5-DMOBA) and also learning how to run TLC before I retried it.

The acetaldehyde is ever so slightly more annoying to get but Is probably roughly the same cost (maybe a little more than that) as the formalin solution - I did quickly figure out it’s a better idea to add it to a methanol solution given it’s boiling point!

Can I ask if you run it exactly the same as the formaldehyde /reductive animation - as in do you still do multiple ‘rounds’ of additions of acetaldehyde and then NaBH4? It’s nice to finally meet someone who has done this…if you could add ANY detail at all, it would be REALLY useful.

For me; n,n-DMT is cool and everything and it was the reason I started getting into chemistry - HOWEVER, it was far from the only reason and I would probably say the search for a way to make DET piqued my interest WAY MORE than DMT, given the ease of its extraction from mimosa…

So yeah, given this is basically the whole reason I ‘got into’ chemistry - if you could add ANY details of your experience whatsoever, that would REALLY help me…

Thanks for confirming it can be done though - this knowledge, along with my experience of the DMT synth and what I have come to learn from trying a few syntheses as well as reading A LOT should help me on my quest!

I’m SO GLAD I found out about reductive animation of tryptamine using aldehydes/ketones.
Before I read about this way I was looking at that synthesis Hamilton Morris added into his DMT episode where the guy actually sort of does a reductive animation, however, iv since heard that it doesn’t even work and they had to ‘fake’ the last crystallisation step.
I even got all the RANDOM solvents he was using (I think he started it in DCM and then used DCE? At one stage - anyway it sort of follows this method however, I don’t think he even used an ice bath (could be wrong as iv not watched it for like a year since I started this quest)

So sorry for the long post; it’s exciting when someone confirms something you have been wanting to do for a year or so!

In other words, although I practiced by making DMT, I REALLY want DET.

Oh also is the work up the same as with n,n-DMT?

Do you simply finish the RXN and then quench it in a water bath, then basify and extract with DCM, then RE-x with n-heptane?

Or do you need to do an A/B type extraction of the DET?
Any details on this would be great…
 

gnbarsh3463_11

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I don't mind sharing synthesis notes, but the forum won't let me. Every time I try to post, there is an error. DM if you are still interested.
 

Rabidreject

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I have two questions….from your DM.

1. Did you make a methanol/acetaldehyde solution to add to the addition funnel to make it less reactive meaning better temp control and less evaporation?

2. In your workup, I assume the K2CO3 was used to make the solution basic before you extracted? Could you just as easily substitute that for KOH or NaOH and then dry it using either MgSO4 or even CaCl2 or something? If its that you used that just because you had it and it did multiple things at once, rather than it needing to specifically be K2CO3 do make me aware coz I was planning to work it up just by basifying using either NaOH or MgSO4 - essentially the exact same workup for DMT…in other words, it seems silly to buy a base I don’t have when I have substitutes…
 
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