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View Full Version : Pepper to Pyridine - Dehydrogenation of Piperidine


MrSparkle
2008-07-12, 13:12
I read that "piperidine can be changed into pyridine when sulphuric acid at 300° C. (572° F.) or gentle oxidizing agents act upon it."

Is this within the capabilities of the layman? A simple thermolytic reaction how hard can it be?

wolfy_9005
2008-07-12, 14:51
Sulfuric Acid at 300C isnt something you want to play around with.

Unless my memory isnt working, isnt pyridine used for making codeine into morphine or something like that?(dont quote me on this.....)

MrSparkle
2008-07-12, 14:54
Yeah it can be used to demethylate codeine. Heres another potential route swim found
Piperidine may be rapidly converted into pyridine using palladium(II) Chloride or tetrachloropalladate(II) ion in aqueous medium at pH 10-11 and in the absence of oxygen. Cyclohexanone may be aromatized under the same conditions, although more slowly. The products fromo-cyclohexenylcyclohexanone are also described.
sounds alot safer than heating sulfuric acid to 300C. OTC availability may be an issue though.

Damn is it really that simple to aromatisize piperidine? Piperidine + PdCl2 in a basic aqueous medium? Swims no chemist but that sounds pretty OTC and simple to him. Absence of oxygen? Swim assumes that means performing the reaction in vacuo.

On a side not what would you get if you aromatisized cyclohexane? Phenol?

fcknut
2008-07-12, 16:05
Absence of oxygen? Swim assumes that means performing the reaction in vacuo.

Generally speaking, "in the absence of oxygen" means "in an inert atmosphere" i.e. you do it under nitrogen or argon or a similarly inert gas



On a side not what would you get if you aromatisized cyclohexane? Phenol?

cyclohexane?

benzene


cyclohexanone or cyclohexanol would lead to phenol

Von Bass
2008-07-12, 17:24
Piperidine + PdCl2 in a basic aqueous medium? Swims no chemist but that sounds pretty OTC and simple to him. Absence of oxygen?

Palladium chloride is notoriously hard to find nowadays. There are still sources, but I can only see 'inquiry' type ones, nothing truly OTC. It's also expensive, probably more so than just buying pyridine, which I've seen a lot more readily available.

Absence of oxygen is probably going to mean under-a-stream-of-insert-inert-gas-here. Unless your vacuum source is going to suck nitrogen rather than air ;)

MrSparkle
2008-07-12, 19:12
Elemental palladium can be had OTC and can be converted into salts. Only the extremely determined last in this hobby. Swim believes in a world where everything can be made from OTC chemicals even if it requires going back 20 steps.

FullMetalJacket
2008-07-13, 04:25
One must wonder, however, why on earth you'd be pushing your piperadine to pyridine when there are far cooler things to do with piperidine, and far easier ways to get pyridine.

MrSparkle
2008-07-13, 18:51
Piperidine is easy as piss to get. If you know an easier way to get pyridine OTC let me know.

Von Bass
2008-07-13, 19:34
Piperidine is easy as piss to get.

Are you talking about doing a piperine extraction, and then heading to piperidine via hydrolysis? Because everyone who I've seen who's attempted the reaction first hand says that piperic acid is plausible, but piperidine is much harder.

If you know an easier way to get pyridine OTC let me know.

Niacin decarboxylation looks more plausible, but I've never seen of anyone who's done it.

The cost of buying elemental palladium, and the amount of pepper required to extract a decent amount of piperidine to then convert to pyridine makes it seem completely pointless and uneconomic right off the bat. Sorry, its possible, but there appear to be better ways, like just getting a friend to order some pyridine.

MrSparkle
2008-07-13, 21:28
You'd be surprised Von Bass. Piperine -> Piperidine can be done.

Your right Von Bass its far from simple but if it can be done OTC then why the hell not. Swim has tons of addresses to deliver to the problem is finding someone with a credit card willing to use it to order chemicals.

DiamondX
2008-07-14, 07:42
You'd be surprised Von Bass. Piperine -> Piperidine can be done.

Your right Von Bass its far from simple but if it can be done OTC then why the hell not. Swim has tons of addresses to deliver to the problem is finding someone with a credit card willing to use it to order chemicals.

Why not get one of those visa gift cards at the supermarket/grocery store? Just fill up with cash. I think they charge you if it doesn't get used for a few months, but that shouldn't be a problem.

Von Bass
2008-07-14, 15:50
You'd be surprised Von Bass. Piperine -> Piperidine can be done.

Your right Von Bass its far from simple but if it can be done OTC then why the hell not. Swim has tons of addresses to deliver to the problem is finding someone with a credit card willing to use it to order chemicals.

Oh I agree, it can be done, it would be pleasingly difficult to ban the purchasing of pepper. This therefore at least allows easy access to piperine, with a few solvents. But once you've got to piperidine, especially if in the amounts required for a decent conversion to pyridine... well... if nitroethane were available I imagine a person would be more tempted to head in a different direction with their materials. ;)

I also seem to recall clean piperine can just be bought from health food shops for some insane reason. Masochistic food eaters I assume.

I would, of course, love to see SWIMS' experiments, if he or she chooses to do so, it would be really interesting, and I'd gladly be proven entirely wrong about the feasibility if it meant someone had discovered an OTC route to pyridine!

So good luck if you choose to attempt such syntheses. :)

fcknut
2008-07-14, 16:51
I also seem to recall clean piperine can just be bought from health food shops for some insane reason. Masochistic food eaters I assume.




Indeed... and not really all that pricey, though whether this option is available in the good old U S of A, I don't know...

However, I'm in full agreement in that there are much better things to with large molcule of high functional density than their decomposition, although I'm sure one could incorporate both of these ideas at once if they thought about it hard enough... ;)

stateofhack
2008-07-14, 16:53
Can we keep this on the topic and no to criminal activities? We have other forums for this.

MrSparkle can you please post the full ref/paper of the work you cited? I would be very interested to see it!

fcknut
2008-07-14, 17:06
Can we keep this on the topic and no to criminal activities? We have other forums for this.

MrSparkle can you please post the full ref/paper of the work you cited? I would be very interested to see it!

http://www.henriettesherbal.com/eclectic/usdisp/piper.html

Try here, I'm sure I could hazard a guess as to what the A. J. P. is, but I can't be assed atm to actually go ahead and find it...

Phanatic
2008-07-22, 15:24
I also seem to recall clean piperine can just be bought from health food shops for some insane reason. Masochistic food eaters I assume.


http://www.delano.com/Articles/piperine-multiplies.html

Apparantly piperine improves the bioavailability of certain supplements. IIRC JoePedo used this or went a similiar pathway with his muscle-building regimen because it increases your insulin sensitivity.

stateofhack
2008-07-22, 18:33
http://www.delano.com/Articles/piperine-multiplies.html

Apparantly piperine improves the bioavailability of certain supplements. IIRC JoePedo used this or went a similiar pathway with his muscle-building regimen because it increases your insulin sensitivity.

I have seen in actually in a pharmacy (30% mixed with some stuff). But you can buy it in pounds on the internet, so no problem :) Now you have some pyridine for you nasty deed's :)

Capt Obvious
2008-07-29, 23:54
All mentions to the conversion with sulfuric acid are based on this. Not what you were hoping for, is it?
http://mihd.net/zp7xu34

stateofhack
2008-07-30, 09:09
All mentions to the conversion with sulfuric acid are based on this. Not what you were hoping for, is it?
http://mihd.net/zp7xu34

Actually i speak a bit of german and i will try to get some of this sorted out with the help of a german friend of mine!

thanks!