Fairly Novel DMT Attempt

[cilliersb]

Indole-3-carbinol (1) can be had for next to nothing on the web. Reacting this with HX (well HI or HBr) will form indole-3-methyliodide. (2)

Purchase some 2-Dimethylaminoethyl chloride Hydrochloride (3) from your chem supp. react the freebase of (3) with Mg and we are on for grignard. (resulting in DMT)

Now the older beez will be more knowledgable on such things, but this bee will make a project out of it once viability has been confirmed.

Any ideas guys?

[Lilienthal]

Indole-carbinol is 3-(hydroxymethyl)indole. Oh, and you should try to count the carbons of your product...

[cilliersb]

I know what Indole-3-Carbinol is, else I wouldn't have suggested this.

Sorry, DimethylAminoMethyl Chloride Hydrochloride is the reagent not DimethylAminoEthyl Chloride Hydrochloride.
 
Still a new method of DMT production, unless nobody has the time to say why it wouldn't work.
Sorry Guys

[Lilienthal]

How would you prepare the chloromethyl-dimethylamine? Under which conditions would you let it react? Are there similar published reactions?

What do you expect from us? If you want to start a fruitful discussion you have to prepare yourself (and us)!

E.g. it took a while of my (and probably others) time to find out that indole-carbinole is  hydroxymethyl-indole. If you did know it why didn't you post it???

[Rhodium]

Me₂CH₂Cl is only $150 for 5 grams... And no practical amateur prep route exist.

[Lilienthal]

It is not in the Aldrich catalog and not in Chemfinder. Where did you find it? And how do you know that there is no easy synth?

[Rhodium]

Beilstein Crossfire said it was sold by Aldrich as 48,389-3 N,N-Dimethylmethyleneammonium chloride, CAS [30354-18-8] - it is the chloro analog of Eschenmoser's Salt, which is the Iodide.

Beilstein only listed really yummy synths, such as the reaction of Me₂NH with Cl-CH₂-O-SO₃H and similar toxic, corrosive and carcinogenic brews.

You probably didn't find it as Chemfinder didn't check for the methyleneimine tautomer.

[Lilienthal]

Oh, that's a completely different compound. Actually it's not even a tautomer    but the dehydrohalogenated chloride of our compound. I don't think that there could be an equilibrium between them.

[Rhodium]

Isn't a "dehydrohalogenated hydrochloride" per definition a sort of tautomer (if not, what is the relation then called, as it is most definitely reversible)? Anyhow, Beilstein crossfire use both forms interchangeably, so I trusted them...

[Lilienthal]

Tautomers are interconvertable by a formal migration of one hydrogen.
Beilstein doesn't list both chemicals as identical or equivalent. Both compounds have similar trivial names and the trivial english chemical nomenclature has its weakness... Since Beilstein is full of crappy entrances I think it's just a mistake, made by some unmotivated students while typing in the data or made in some ancient publications.

[Teon]

I am not a stupid person. That being said, you guys make my brain throb.