The Vespiary

The Hive => Tryptamine Chemistry => Topic started by: Bandil on May 01, 2002, 01:18:00 PM

Title: The role of AA in shulgin N,N-dialkylations
Post by: Bandil on May 01, 2002, 01:18:00 PM

Hi!

When reading the DPT og DiPT in TiHKAL swim cant help but wonder why he is boiling the product in Acetic anydride? It does not seem to do anything with the product. Swim thinks that i might be to eliminate the Diisopropylethylamine base, but he is not sure?

Can anyone help here? It would be quite nice to avoid using AA as it is quite watches beacuse of those damned heroin pricks :)

Regards
Peter

Title: acetamide
Post by: Lilienthal on May 01, 2002, 04:49:00 PM

Simply to remove unreacted primary and secondary tryptamines as their non-basic acetamides.

Title: alternative?
Post by: hypo on May 01, 2002, 08:59:00 PM

could the same be achieved by refluxing with excess acetic acid and toluene on a dean-stark? what about formic acid?

Title: primary and secondary amines ?
Post by: Sunlight on May 01, 2002, 10:27:00 PM

I've always thought the anhydride will form n-alkyl formyl tryptamines, won't it ?

Title: Why AA?
Post by: Rhodium on May 02, 2002, 12:32:00 AM

Anhydride of what? Formic anhydride does not exist, and acetic anhydride will form the N-acetyl derivative of tryptamine and N-alkyltryptamines, and leaving dialkyltryptamines alone - after this treatment only dialkyltryptamines will carry through an acid/base extraction while less substituted tryptamines will be converted to acetyl-amides and can be removed from the product amine easily.

Title: Yes, yes, acetic anhydride
Post by: Sunlight on May 02, 2002, 02:12:00 PM

Yes, yes, acetic anhydride, I was a bit stoned... acetamide , not formamide.

Title: No
Post by: Lilienthal on May 02, 2002, 04:25:00 PM

edited (not Bwiti of course):
Hypo: No

Title: Bwiti ?
Post by: Sunlight on May 02, 2002, 11:47:00 PM

Did you want to mean Hypo ? with my mistake and your "no" this starts to be confusing...