tryptophan decarboxylation questions

[leaf12]

I have two questions about two methods of decarboxylation:

https://www.thevespiary.org/rhodium/Rhodium/chemistry/tryptophan.html

- Decarb in diphenylether

Is it really necessary that this reaction is carried out under nitrogen(inert) atmosphere? If it does, do you have any tips for doing this when you don't have a cylinder of N2?

- Decarb in cyclohexanol with 2-Cyclohexen-1-one katalyst.

Does anyone knows a way to make this one? I searched the forum and Organic Syntheses but found nothing?
Some kind of partial dehydrogenation of cyclohexanone?

[elfspice]

the cyclohexanol/cyclohexenone decarboxylation works via the cyclohexenone's ketone group inducing the formation of carbon dioxide from the COOH, and the remaining hydrogen then goes onto the carbon chain.

The diphenylether decarboxylation works simply by high temperatures, sufficient heat and the acid groups own keto-radical decarboxylates the thing by itself. This reaction has to be done with inert atmosphere because high temperatures also increase the likelihood of oxidation, resulting in broken molecules.

there are numerous other mechanisms reported here on the hive

I experimented once with amino acids extracted from pills with acetone in a sealed container (pressure pipe) raised to 250 degrees in an oven, dangerous... yes, but there did seem to be some amount of reaction occurring in the limited experiments done, perhaps adding CO2 to the atmosphere of the pipe would help here too, as would having a pipe constructed of high grade stainless steel with a pressure release valve attached to a vent tube to remove the vented acetone (in the case of excessive pressure) from the heating device and clear of the operator.

[elfspice]

yes, don't try it at home kiddies, acetone, while not as explosive as hexane or butane etc, is flammable, and a domestic galvanised pipe is not neccessarily engineered to take the pressure that could develop - and filling it too high would also risk a liquid pressure buildup which would definitely cause a rupture.

[Lilienthal]

It is absolutely  suicidal to run a gas developing reaction in a closed environment without professional eqipment.

[leaf12]

Ok, we won't try this one than .

But does anyone has ideas on how to make 2-Cyclohexen-1-one???

Thanks in advance.

[Rhodium]

2-Cyclohexen-1-one can be found as an impurity in technical grade cyclohexanol, so running the decarboxylation in cheap-ass refluxing old cyclohexanol will work.

Reference:

A Novel Decarboxylation of alpha-Amino Acids
M. Hashimoto

Chem. Lett., 893-896 (1986)

(https://www.thevespiary.org/rhodium/Rhodium/chemistry/trp.decarbox.enone.html)

[leaf12]

Hmmm I doubt if Merck synthesis-grade will work then, but we can try..

[Psi_Locybe]

You sound almost as if you're about to make the horiffic mistake of spending sums of money to put your name on the list as a purchaser of chemicals...

So... you need a decently-boiling ketone? 

Ever hear of tansy?

Its oil is about 77% thujone.  Sure, it boils kinda right-at-the-line - about 201c, if I recall correctly - but I can assure you from whatever-personal-experiences-are-lawful that, if ya just toss a little oil of tanacetum into a pot filled with peanut oil & tryptophan, stick the lid on, and try-oh-try not to let the thing burst into flames, it'll work at *least* semi-decently.

BTW...

...how much did you pay for your tryptophan?  Too much?

Grab 5lbs of sunflower seeds.
Make a "giant cauldron-full-of-tea"
Pour yourself a glass.  Don't drink it, because excessive tryptophan intake can have severe side effects (I had no idea where I was, or whether I was masturbating... don't.)  Crash out the tryptophan with about twice the liquid volume of acetone.

::shrug::  Ghetto - but it works.

Oh, btw... if tanacetum ain't in your area - sage is about 70%.  Point a fuckin' search engine at 'wid for refs... NIH in origin, I think, there archived... but fuck I'm senile... so who knows.  *You* check.

Peace.

[Teon]

If the tryptamine were suspeneded in a mixture of 1,2,3,4-Tetrahydronaphthalene and acetone would it still be necessary to react under a nitrogenous atmosphere?

[chemotype]

What about a Barton radical decarboxylation?  Form the acid chloride, react with N-hydroxypyridine-2-thione & irradiate.