foxy2 (Hive Bee)
06-14-00 15:38
No 17344
      Quant Salts  Bookmark   

Anyone have heard of someone reduceing n,n,n-Trimethyltryptamine salts (or their ethyl/propyl homologues)
Shulgins yeilds were pathetically low.

I have this from rev Drone

J. G. Whitney et al., J. Med. Chem. 13, 254 1970: The reaction follows the sequence 1. quaternization of methyl-amantadine with methyl iodide / NaHCO3 / MeOH, reflux 16 h. 2. reflux of the quaternary salt with ethanolamine for 15 min.

"Yes, admittedly the quaternary salt is formed here as an intermediate, but treating it with ethanolamine for 15 minutes is hardly a difficult or unreasonable procedure. I think you're just trying to be difficult here."

Anyone done this?  What are the chem wizards thoughts on useing ""Di""ethanol amine instead of ethanol amine for this.
Rhodium said it should work but i don't know if he noticed the ""Di"" stuck in there.
I have alot of diethanolamine sitting here that wants to be used and abused.  I figure an excess with a longer reflux period should accomplish the goal just like ethanol amine.

One step closer to the sweet dreams

"The best place for a pig is in the fryin pan"
(Chief Bee)
06-14-00 19:44
No 17408
      Re: Quant Salts  Bookmark   

In my opinion, diethanolamine wouldn't work that good. The mechanism is based on the fact that the ethanolamine is present in excess over your quaternary amine, and thus the "extra" alkyl group is preferably transferred to the amine function of the ethanolamine. Diethanolamine already has two substituents, and will probably not work as efficiently (it is also more sterically hindered to perform the reaction).

Note: It is always the shortest alkyl group that is transferred, so if you had butylpropyletylmetylammonium chloride, only the methyl group would be transferred from the quaternary salt to ethanolamine, giving ethanolmethylamine (HO-CH2-CH2-NH-CH3) and butylpropyletylamine.