DMT synthese via quaternary ammoniumsalt

[freakyDMT]

In THIKAL page 412 tryptamine is reacted with iodomethane in absolute ethanol (or isopropylalcohol) to form the quaternary salt of DMT.
3 grams of tryptamine yields 1.81 grams of the Me₃I salt.
thats a yield of not more than circa 29%.
the rest is tryptamine,NMT and traces of DMT.
shulgin says that it is possible to get the tryptamine out of the filtrate so it can be reused again,by using ether.
does anybody know how to do this?
is it possible to better this low yield,i'm thinking at the route from LSD-25 & tryptamine syntheses from otto snow,page 67 by adding anhydrous sodiumcarbonate,does this better the yield?
if so this an easy route to DMT by using ethanolamine!

[Lilienthal]

Sodium carbonate wouldn't change the relative amount of the products. But adding > 3 equivalents methyl iodide would give quantitative yields.

[freakyDMT]

i don't understand this,you say i have to ad 3 mol MeI for each mol of tryptamine,that means for 3 grams of tryptamine
i have to ad 8 grams of MeI,that is 2 grams less than in THIKAL,or do i see this wrong,can you help me out?

[Lilienthal]

Yields might be better with longer reaction times, a larger excess methyl iodide, the use of an aprotic polar solvent, a HI scavenging base, prevention of NMe3 elimination by use of lower temperatures and weaker bases, and the use of a better work-up procedure.

I don't have the time to search for the procedure you are talking about, please provide a link the next time you want people help you.

In general there is no reason not to come close to 100% in such a reaction...

[freakyDMT]

sorry that i did'nt give you enoff info on this syntheseroute,but you have to understand i'm just new here,i still have to learn.
but about the synthese:
the first route is from THIKAL page 412,
To a stirred solution of 3 g tryptamine in 30 ml IPA there was added 10g methyliodide (tryptamine/methyliodide 1:3,75).
cream colored solids appeared immediately and,after 12 h stirring st roomtemperature,these were removed by filtration,washed twice with warm IPA and airdried to constant weight.
there was obtained 1.81 g N,N,N-trimethyltryptammoniumiodide
than shulgin says that the the unreacted tryptamine can be removed on its ether insolubility.
i think the first thing to do is to concentrate the fitrate
and cool.
the second fase is to extract the second fitrate with an solvent for example ethylacetate and dilute the extract with ether to kristallize the unreacted tryptamine for re-use.
this the first possebility
the second one is to optimize the reaction.
large amound MeI,mayby other solvent.
i do know that the second route,
from otto snow:
1.6 gram tryptamine is mixed in 36 ml anhydrous ethanol.
6 gram of MeI containing 5.4 gram of anhydrous sodiumcarbonate are added to the solution and refluxed on a hot waterbath for 5 h.
the hot solution is then rapidly suction filtered,alcohol is added to the residu and heated to boiling and rapid suctionfiltered.
the filtrate is concentrated under reduced pressure.
large colorless needles o trimethyl-beta-3-indolyl-etyl-ammonium-iodide precipitate and are suction filtered.
the solution is reduced further to crystallize more trimethyl-beta-3-idolyl-ethyl-ammonium-iodide.
but he does not give any yield,but this one sounds much beter.
i do know that this one was first invented by a german,his name is wieland,annalen der chemie(1934) 513:1-25, but i can't find the original paper.
maybe it is worthwill to extract the unreacted tryptamine?by the way what does HI scavenging base means?  

[Rhodium]

I am not commenting on this procedure in particular, but in general Otto Snow very often have no clue what he is talking about. If his books were threads at the Hive, I would have rated a lot of the sections as either "insignificant" or "off topic". There are not so many blatant errors in the book though, but I'd say the reason for that is that he hasn't written much of the books himself (except the political rants), it is largely a book with collected references. But - as he has neither chosen the best references nor tried to make as comprehensive compilation of all pertinent ones, I really wonder how he made his selection before writing the books - to me it seems like he gathered them more or less at random for each featured synthetic transformation.

He has found quite a few lesser known procedures which are real gems, but that is what is to be expected from a random pick on the other hand. Too bad that you need to retrieve all the mentioned articles first to discover which ones are great or not, as Otto himself give few or no hints which ones are the most important.