Reaction of N,N‑Dimethyltryptamine with Dichloromethane Under Common Experimental Conditions

[benzyme]

I recently did a run, extracted with aqueous NaOH and DCM, and ran the recrystallized product through the mass spec; my results were consistent with those in the attached paper (product 10); although I did extract quickly (0 mins), the exothermic conditions lead to boiling of the dcm in the sep funnel, and of course, heat catalyzes adduct formation. M.P. is 63-66C; I will experiment on recrystallizing under vacuum, maybe short-path, to eliminate the n-chloromethyl adduct. Another option would be to just salt it.

 

[neurobloom]

Thank you for this. both DCM and chloroform are my solvents of choice for extracting tryptamines. I always had the concern over the formation of N-
chloromethyl-N,N-dimethyltryptamine chloride.

Good thing that I always waited for the based solution to cool of to room temperature before adding the chlorinated solvent. I was trying to avoid boiling the solvent and avoid inhaling it

Nice work 8)

 

[benzyme]

thanks

I'm considering switching to ethyl ether, benzene, or naphtha, and waiting for the basified solution to cool (I'm not a patient person). Tried EtOAc, not a fan.

 

[Twilight Person]

I once tried Ether but it catches damn too much water throughout the whole process ...

Already liquid-extracting will leave a lot of water inside behind and then even more coming while evaporation ...

So seems like we can all be pretty happy about how Alkanes catch it up at high temperatures and will nicely freeze precipitate all those goodies again ...!

Toluene is of course also pretty strong at room temperature and xylene has no benefits over it in a chemical sense. So why do people use Xylene instead of Toluene when it comes to room temperature pulls if it will evaporate MUCH slower? Is it so much more accessible in the US?

 

[artificer]

Xylene is toxic, but slightly less than toluene. I remember reading that there was a push to replace toluene with xylene in hardware stores for this reason. I did find a old dusty can of toluene at back of shelf once, but I notice xylene in stores much more frequently. To obtain DMT fumarate, FASA can be applied to xylene or toluene just the same, and avoid the fume issue altogether.

 

[famine]

I once tried Ether but it catches damn too much water throughout the whole process ...

Already liquid-extracting will leave a lot of water inside behind and then even more coming while evaporation ...

So seems like we can all be pretty happy about how Alkanes catch it up at high temperatures and will nicely freeze precipitate all those goodies again ...!

Toluene is of course also pretty strong at room temperature and xylene has no benefits over it in a chemical sense. So why do people use Xylene instead of Toluene when it comes to room temperature pulls if it will evaporate MUCH slower? Is it so much more accessible in the US?

Ether is fine, just dry it under MgSO4 before evaporating. The aqueous layer grabs too much ethyl acetate for it to be a worth while extracting solvent though

 

[downwardsfromzero]

[...]Tried EtOAc, not a fan.

I'm guessing this is a mutual solubility issue with water? Might be why it has gained favour in limeteks rather than liq/liq etractions.

Ether is fine, just dry it under MgSO4 before evaporating. The aqueous layer grabs too much ethyl acetate for it to be a worth while extracting solvent though

Did you mean ether or ethyl acetate? Maybe both?

 

[benzyme]

ether works fine for me, but I decided I'll stick to dcm or dce, and use the ether with pet ether/hexanes to re-x.

 

[famine]

[...]Tried EtOAc, not a fan.

I'm guessing this is a mutual solubility issue with water? Might be why it has gained favour in limeteks rather than liq/liq etractions.

Ether is fine, just dry it under MgSO4 before evaporating. The aqueous layer grabs too much ethyl acetate for it to be a worth while extracting solvent though

Did you mean ether or ethyl acetate? Maybe both?

Sorry meant et2o when I said ether