Will this 5-MeO-Tryptamine synthesis work?

[Jeffrey B.]

200ml of butanol was added to an rbf setup for reflux with an allihn condenser. 10g of NaOH was added and the solution was brought up to 80C. 25g of melatonin was added gradually. When done, the solution was brought up to 110C and left there for 3 hours. The solution was checked every 30 minutes.
At one point the solution became very thick and stirring stopped. Butanol was added to redissolve the slurry. After 3 hours, the solution was put off heat and 80ml of water was added and the solution was left to stir for 20 minutes. The water layer was discarded. Leftover butanol was concentrated and became very viscous. Isopropyl alcohol was added to redissolve the slurry. This mixture was diluted with Et2O and put in the freezer overnight. Roughly 22g of yellowish 5-MeO-Tryptamine freebase was obtained which is a yield of 88%.

 

[Jeffrey B.]

I would also like to know why nobody on here mentions the sodium dithionite wich is clearly listed as a non-optional ingredient in the paper below
[paper I have seen]

 

[HerrHaber]

Dithionite is required as a reducing agent and the function is to destroy an intermediate, for sure it can be replaced with other agents of similar strength must look out but Dithionite is usually available. My best melatonin hydrolysis by far was done with KOH/MeOH and I discovered that upon partial removal of solvent under light vacuum with a conventional apparatus it conveniently precipitated as I removed the mantle instantly.

 

[Jeffrey B.]

Dithionite is required as a reducing agent and the function is to destroy an intermediate, for sure it can be replaced with other agents of similar strength must look out but Dithionite is usually available. My best melatonin hydrolysis by far was done with KOH/MeOH and I discovered that upon partial removal of solvent under light vacuum with a conventional apparatus it conveniently precipitated as I removed the mantle instantly.

HerrHaberThanks! I guess I'll add Dithionite to my shopping list!
Could you please go into detail about what would happen if I didn't use it?
I'm also pretty sure this reaction would work with NaOH (I already have it) as well as with KOH, but how much NaOH do I have to use?
And lastly, how did you separate the residual KOH and other impurities from the product?
In the paper I've seen it says that a non-polar alcohol with 4 - 8 carbons is required for separation after water was added to dissolve the impurities.
Thanks in advance!

 

[HerrHaber]

it is basic hydrolysis but product has an upper limit of pH it can withstand that is unadvised to surpass carbonates are safer in this regard.

 

[Jeffrey B.]

it is basic hydrolysis but product has an upper limit of pH it can withstand that is unadvised to surpass carbonates are safer in this regard.

HerrHaberIf possible, could you please tell me what pH should I achieve in this hydrolysis so that my end product won't immediately decompose?
An also what would happen if I didn't use dithionite, as other senthesis procedures I've seen don't seem to mention it

 

[HerrHaber]

pH as far as I remember can go above 11 well but over 12 it's an unnecessary compromise and Yields I bet they drop. Same with temperature as well as with strength and concentration of acids (in my opinion the F.B. can stay in a freezer for some weeks maybe months so you don't need to freebase the hydrochloride every time. It all depends on your intention with it and wether or not you will use the whole amount to make the same product in three or even 2 batches.