Author Topic: Catalytic Hydrogenation for mescaline  (Read 3912 times)

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  • Guest
Patent. 2835700
« Reply #20 on: May 12, 2002, 11:11:00 AM »
The Iodation-Bromination looks possible, via US. Pat. 2,835,700. Coulumn 4, Wherein Tyrosine is Iodated.

I'm concerned most about the methylation step. Wherein the Na/K phenolate, might be reacted with a controlled amount of Methyl Iodide. True, it might like to methylate that amino function if unprotected.

But, would it prefer that amino, over interacting with those delicious Alkalie Metal phenolates, and carboxylates?

What do you think?


  • Guest
Apparatus....Not that simple!
« Reply #21 on: May 12, 2002, 01:55:00 PM »
Aside from poor yields, there were scaling problem; These reductions can require a lot of current. That's not to say a clever Bee, couldn't make a breakthrough.

Master Researcher, Polyethylene Sam, has a topic posted just below this one. It is on electroreductions. Try posts 299552 and 306860. He claims the cited patents contain apparatus construction details.

Good luck...........zed


  • Guest
The Electrolytic Apparatus
« Reply #22 on: May 12, 2002, 10:01:00 PM »

Aside from poor yields, there were scaling problem; These reductions can require a lot of current. That's not to say a clever Bee, couldn't make a breakthrough.

Unless the clever bee manages to raise the cell resistance to such a value that he/she can use lower currents with appropriate voltages to effect the reduction, although having to wait longer. Details on apparatus for reducing nitrostyrenes efficiently has been around since the thirties, in fact the translation of the article is located at

, the illustration has been posted here on the Hive. But please, share some information on your own apparatus, even if it didn't work so well. There is very little information on experiments conducted by bees and the key to success is avoiding the mistakes.


  • Guest
Sorry Moo!
« Reply #23 on: May 13, 2002, 12:12:00 PM »
Sorry Moo, a couple of fellow Bees built the apparatus. I didn't build or design the apparatus myself, I didn't own it, and it was a long time ago.

It was copied from a design reported in literature. It was about the size of a car battery, and contained a series of flat metal plates. I don't remember a lot more about it.

It wasn't working well, there was talk of needing a $1,000 power supply, and It's ~15% yields, were disheartening. As I recall, there was also, gas build up on the electrodes, which interfered with performance....a problem which Sam's patent's, rotating electrode with wiper might help solve.

I was involved with this project for reasons other than genius at electrochemistry. I had other talents.

Anyway, reducing agents were readily available at that time, and there were more rewarding projects awaiting.

Electroreduction would have been nice, but it was a sticky problem.

I'm afraid you need someone who is well versed in this arcane craft, and has successfully practiced electroreduction. Wish I could be more helpful, but I'm not the guy.

I wish you well .........................zed

P.S. We would have been happy to accept longer reaction times. But, longer reaction times did not seem to help yields. We concluded that if we overcame other problems, we would still need a huge power supply, to provide the current density needed. Further, even the literature reported yields, for the ring substituted phenethylamines that we were interested in, were modest.

Were I to take on such a project, I would try to make sure there was some payoff, even if things went poorly.

I used to find a co-operative chemistry/physics professor, create my own independent studies course, use free college equiptment, and reagents, get college credits, and collect every cent of student grant money I could.

I then restricted myself to legal projects, that might have other applications. My projects usually failed, but my grades were good, it didn't cost me much, and the only stress involved was in trying to accomplish the impossible.

It is quite possible, none of this applies to you, but I guess my point is, this might be a pretty demanding project.


  • Guest
oxime reduction
« Reply #24 on: May 15, 2002, 12:55:00 AM »
I found this in a book today.  It seems oximes can be reduced catalytically.
The hardest thing to explain is the obvious


  • Guest
« Reply #25 on: May 15, 2002, 08:12:00 PM »
Sam: That link doesn't work for people not logged into webshots.


  • Guest
Chemtext3 folder
« Reply #26 on: May 16, 2002, 02:40:00 AM »
OK.  Try going here

and look at the last picture in the Chemtext3 folder.
The hardest thing to explain is the obvious


  • Guest
« Reply #27 on: May 16, 2002, 12:54:00 PM »
Perhaps something is poisoning hest's catalyst. The reduction of Nitro-olefin to Oxime is very easy. The reduction of the Oxime, is less easy.

A Catalyst that quickly reduces the Nitro-olefin, might none-the-less be too compromised, to reduce the Oxime.

While there are few viable reports of reducing Nitro-propenylbenzenes, directly to Amines via PtorPd/H2....There have been many reports of B-Nitro-Styrenes being reduced to Phenyethylamines by this means. Maybe something is wrong.

Of course, it is probably possible, to take the Aldehydes, or Ketones that are easily produced by this reduction, and hydrogenated them with Benzylamine, to produce the Psychedelic N-unsubstituted Amphetamines or Phenethylamines desired. The reduction first produces, the N-Benzylamine, which I believe is cleaved by reduction to toluene, and the desired Amine.

It might avoid hydrides, and produce good yields.

TFSE still doesn't like me, but I'll see if I can find a reference.


  • Guest
Ah, TFSE does work!
« Reply #28 on: May 16, 2002, 02:08:00 PM »
Ah! Zed's Megalomaniacal Euphoria, was causing zed to type his own name in the user Id box. Since this proceedure could only call up items that zed had posted himself, this usually resulted in 0 results. It is much more entertaining when that space is left blank.


  • Guest
« Reply #29 on: May 16, 2002, 06:17:00 PM »
The Pd/C was just fine. several batch's from aldrich was used. They all work in different reductions.
The redution off nitroethens is not that common. A quick beilsten end up with 30-40 hits (200-300for the LAH) And they usual have low yeald (<60%) or a HIGH Pd/C load (g/g)


  • Guest
off topic
« Reply #30 on: May 16, 2002, 07:45:00 PM »
Is there a rehab to the Hive ??


  • Guest
Hest, In a related matter.
« Reply #31 on: May 17, 2002, 11:30:00 AM »
Hest, in a related matter, this Oxime resistance to reduction might actually be useful. A few bees have expressed interest in Indole-3-acetaldehyde as a DMT precurser, but producing this material via Oxidation of Tryptophane is touchy. It might be produced as follows.

The sequence is:

1. Indole.....To Indole-3-Carboxaldehyde.

2. Carboxaldehyde+Nitromethane.....To the Indole Analog of B-Nitrostyrene.

3. Followed by reduction of the Nitro-olefin to Oxime. This should produce the Oxime of Indole-3-Acetaldehyde.

The advantage being that fairly large amounts of this material, might be synthesised in this manner; the reagents, and reactions are well known, and proceed in reasonable yields.

Shulgin provides pertinent reaction information in his #48 alpha-MT synthesis recorded in Tihkal.

You have been battling to reduce the Oxime of a phenylacetaldehyde. Were your craft applied to Indoles, the Oxime of Indoleacetaldehyde would actually be your goal.

When your current battle is over, that hydrogenator, might be used for such an experiment.

Warmest Regards .................................Zed