[LeeA]

I apologize if post in incorrect forum.

In first procedure here https://www.erowid.org/library/books_online/tihkal/tihkal06.shtml
Shulgin forms quaternary iodide salt by reaction MeI with tryptamine. He uses IPA as solvent.

In the past, I'm told that you should use "aprotic solvents to perform alkylation, otherwise nucleophiles will be shielded with solvent protons"... But seems that Shulgin has no problem using IPA (protic solvent)? Would he have high yield with aprotic solvent like ethanol?

Pardon my english, and thank you for helping

[swintarka]

You add pure (neat) MeI to a mixture of amine and IPA. The reaction with the amine is much faster as it is a better nucleophile. The temperature is relatively low, reaction time not so long. I guess that it is still in kinetic (as opposed to thermodynamic) regime, so you can ignore energetic considerations.
An interesting experiment would be another reaction, in closed vial heated to high temperature for long time. Then you could see if that changes the reactivity pattern.

[orgopete]

In the past, I'm told that you should use "aprotic solvents to perform alkylation, otherwise nucleophiles will be shielded with solvent protons"... But seems that Shulgin has no problem using IPA (protic solvent)? Would he have high yield with aprotic solvent like ethanol? [sic, also protic]

Why might this generalization be made? What are the characteristics for which it applies?