Bandil (Hive Bee)
05-01-02 13:18
No 303743
      The role of AA in shulgin N,N-dialkylations  Bookmark   


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 :)

05-01-02 16:49
No 303789
      acetamide  Bookmark   

Simply to remove unreacted primary and secondary tryptamines as their non-basic acetamides.
(Hive Addict)
05-01-02 20:59
No 303873
      alternative?  Bookmark   

could the same be achieved by refluxing with excess acetic acid and toluene on a dean-stark? what about formic acid?
(Pioneer Researcher)
05-01-02 22:27
No 303903
      primary and secondary amines ?  Bookmark   

I've always thought the anhydride will form n-alkyl formyl tryptamines, won't it ?
(Chief Bee)
05-02-02 00:32
No 303941
      Why AA?  Bookmark   

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.
(Pioneer Researcher)
05-02-02 14:12
No 304147
      Yes, yes, acetic anhydride  Bookmark   

Yes, yes, acetic anhydride, I was a bit stoned... acetamide , not formamide.
05-02-02 16:25
No 304177
      No  Bookmark   

edited (not Bwiti of course):
Hypo: No
(Pioneer Researcher)
05-02-02 23:47
No 304313
      Bwiti ?  Bookmark   

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