Dimethyltryptamine (DMT) synthesis from Indole via Indole-3-acetic acid (IAA)

[Joker_55555]

After the heat
Its melting point on the heater was not known, it changes slowly when heated, it is probably also sensitive to humidity. In my opinion, this humidity causes an error in the melting point of the product.

I once poured the product into diethyl ether for solvent-antisolvent extraction after 3 hours of reflux, neutralization, and filtration, and a white precipitate came out, but it didn't even show the reported melting point. I don't know why, but now that I think about it, I think the humidity caused it.
Do you know why?

 

[G.Patton]

After the heat
Its melting point on the heater was not known, it changes slowly when heated, it is probably also sensitive to humidity. In my opinion, this humidity causes an error in the melting point of the product.
View attachment 8497
I once poured the product into diethyl ether for solvent-antisolvent extraction after 3 hours of reflux, neutralization, and filtration, and a white precipitate came out, but it didn't even show the reported melting point. I don't know why, but now that I think about it, I think the humidity caused it.
Do you know why?

Joker_333have you done everything as described here?

 

[Joker_55555]

Have you recrystallized your product? What is the difference in melting point?

G.PattonI did it once, I added ether to methanol and it precipitated, its color was almost white, but its melting point was unknown

 

[G.Patton]

I did it once, I added ether to methanol and it precipitated, its color was almost white, but its melting point was unknown

Joker_333>but its melting point was unknown
check it

 

[farukhocaoglu]

can we get a video on this synthesis, also i am unable to obtain THF, is there anything I can do to synthesize DMT/DET without oxalyl chloride and THF?

 

[G.Patton]

can we get a video on this synthesis, also i am unable to obtain THF, is there anything I can do to synthesize DMT/DET without oxalyl chloride and THF?

farukhocaogluYou can use diethyl ether instead of THF.

Reagents:

• 1 g Indole-3-acetic;
• 0.5 l MeOH;
• 100ml EtOAc;
• 10 ml Concentrated H2SO4;
• 50 g CaCO3 (NaHCO3);
• ~5-6 l distilled water to filling rotavap machine bath;
• 20 ml Dimethylamine (DMA) 40% aqueous solution;
• 1 g LiAlH4;
• 50 ml THF (tetrahydrofuran);
• 50 ml DCM (dichloromethane);
• 200 g Anhydrous MgSO4;

>>>is there anything I can do to synthesize DMT/DET without oxalyl chloride and THF?
Where is oxalylchloride in the list above???

 

[farukhocaoglu]

You can use diethyl ether instead of THF.

>>>is there anything I can do to synthesize DMT/DET without oxalyl chloride and THF?
Where is oxalylchloride in the list above???

G.PattonI was going to follow the original recipe with oxalyl chloride, but I didn't have access to it. I thought I'd write it in case this recipe wasn't possible without THF. Also, thank you for the quick reply.

 

[HerrHaber]

In the first step, the ether is converted to the amine. This stage works well in

G.Pattonester, you mean...

 

[G.Patton]

ester, you mean...

HerrHaberHi, Et2O is Ether.

 

[HerrHaber]

Hi, Et2O is Ether.

G.PattonI thought of the methyl ester of the indole-3-acetic acid, my bad

 

[HerrHaber]

Oxalyl chloride is a diacyl halide and reactive towards the nucleophile (indole), therefore it is very challenging not to have (rather limit) the formation of bis indole-3-ethane-1,2-dione byproduct and the purification of indole-3-glyoxyl-chloride (Kugel-Rohr and near absolute vacuum advised).

 

[Altair]

Can I used indole-3-butyric acid instead of indole-3-acetic acid

 

[HerrHaber]

Can I used indole-3-butyric acid instead of indole-3-acetic acid

Altairwell that is two carbon longer than what you need, indole-3-propionamide can be converted to tryptamine via Hoffman rearrangement reaction (I hope I'm right).

 

[T0lek511]

Where you buy indole?