Hey guys. I need some newb help here; I'm working with decarboxylation of tryptophan to yield tryptamine, and I'm not familiar with this kind of chemistry (at all).
Decarboxylation is very straight forward and easy to carry out, however, tryptamine is so fragile a molecule in the presence of humidity and air, but especially humidity (water and heat). My first attempt came to a solid brown mass at the bottom of the flask, very very viscous oil. I tried to alkylate the amine with ethyl bromide, but the product was so dirty and I couldn't find any sign of the alkylated product by NMR. All I could see was the aromatic hydrogens, really.
I have two very basic but important questions that need some good elaboration. I have been following "student's" follow up on rhodium, which can be viewed here:
However, I did not have vinegar on hand, and used instead a solution of formic acid. The acid does not dissolve very easily, so it was a pain to get the ratios correct. Next what should have been done, as my understanding goes, is that in order to extract the more pure solid, I need to basify to a large pH. Solids should form readily within the solution. What happened with the fumaric acid is that I distilled off the water, and what was left was a clump of viscous oil, and some, what I assume to either be polymerized fumaric acid or melted/degraded acid.
Eventually what I'm getting at here is what is the ideal way for extracting tryptamine from a solution of tryp/turpentine? My impression was the addition of water would cause degradation, but in most cases you need to add a solution of an acid to get the salt - but how do you get crystals of the salt? What is the usual procedure in which people obtain fumaric salts of tryptamines?
Secondly how the fuck do I clean this glass wear? NOTHING takes off this sludge!
Has anyone had success in making diethyltryptamine? It may be easiest if I just go purchase some HCl.
Decarboxylation is very straight forward and easy to carry out, however, tryptamine is so fragile a molecule in the presence of humidity and air, but especially humidity (water and heat). My first attempt came to a solid brown mass at the bottom of the flask, very very viscous oil. I tried to alkylate the amine with ethyl bromide, but the product was so dirty and I couldn't find any sign of the alkylated product by NMR. All I could see was the aromatic hydrogens, really.
I have two very basic but important questions that need some good elaboration. I have been following "student's" follow up on rhodium, which can be viewed here:
Quote
http://www.erowid.org/archive/rhodium/chemistry/tryptophan.html
"...[decarboxylation] -> After sitting overnight there was a clump of yellow crystals in the corner of the flask and solidified dark oil across the bottom. The flask was refrigerated for the day and the orangish mother liquor was poured off.
The impure tryptamine was purified as follows (7). To the flask were added 150 mL of 5% distilled household vinegar along with 5 mL of chloroform (and the flask was briskly swirled until all solid was gone and there was only a little dark brown oil not dissolved in the yellow suspension. The hazy yellow liquid (pH 5-6) upper layer was filtered through a plug of cotton. The small amount of dark brown lower organic layer was extracted with another 10 mL of vinegar, and the resulting upper layer was filtered through the cotton plug. To the combined filtrates were added 5 mL of chloroform and enough sodium bicarbonate (10.58 g) in portions so that further addition caused very little foaming. The flask was swirled thoroughly and the hazy yellow aqueous upper layer was filtered through a fresh plug of cotton. The filtrate was cooled in the freezer for 15 minutes, basified with 12 mL of 25% sodium hydroxide solution, and set back in the freezer for 30 minutes. The solid was dislodged from the sides with a metal scoop and the mixture was filtered through filter paper (9). The flask and crystals were rinsed with 100 mL of ice cold household ammonia in portions (10). The filter paper was pressed between paper towels until damp and set aside to dry. The light yellow crystals weighed 3.64 grams (65% yield).
The turpentine mother liquor from the last reaction, still containing spearmint oil and some tryptamine, was used directly to decarboxylate 7.23 grams of L-tryptophan. This time the reaction took seven hours to become transparent, so apparently some of the catalyst was consumed during the first reaction. This time both the turpentine and the solid product were extracted with vinegar as above, and brought through the same purification process, to give 5.21 grams (92% yield) of light yellow crystals. The combined yield of tryptamine for the last two reactions is 79%. The solid melted at 117-118.5°C (Merck 118°C) and had one tan spot (Rf ~0.1 - 0.2) on silica TLC, eluting with methanol containing ~50 mg of ammonium carbonate."
However, I did not have vinegar on hand, and used instead a solution of formic acid. The acid does not dissolve very easily, so it was a pain to get the ratios correct. Next what should have been done, as my understanding goes, is that in order to extract the more pure solid, I need to basify to a large pH. Solids should form readily within the solution. What happened with the fumaric acid is that I distilled off the water, and what was left was a clump of viscous oil, and some, what I assume to either be polymerized fumaric acid or melted/degraded acid.
Eventually what I'm getting at here is what is the ideal way for extracting tryptamine from a solution of tryp/turpentine? My impression was the addition of water would cause degradation, but in most cases you need to add a solution of an acid to get the salt - but how do you get crystals of the salt? What is the usual procedure in which people obtain fumaric salts of tryptamines?
Secondly how the fuck do I clean this glass wear? NOTHING takes off this sludge!
Has anyone had success in making diethyltryptamine? It may be easiest if I just go purchase some HCl.
Analytical characterisation - thermolytic decarboxylation from tryptophan to tryptamine.pdf