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Compounds With the Most Frustrating Syntheses

Look at this compound patented by Lednicer:

It's a regio-isomer of ethketamine.
Daniel Lednicer, US4113866 (1978 to Upjohn Co).
However if you see the synthesis at the bottom it may be able to simply the process by starting from 1,4-Cyclohexanedione monoethylene acetal [4746-97-8].
www.manchesterorganics.com

1,4-Cyclohexanedione monoethylene acetal

www.manchesterorganics.com www.manchesterorganics.com
Nielsen, Arnold T.; Carpenter, Wayne R. (1965). "1,4-Cyclohexanedione". Organic Syntheses. 45: 25. doi:10.15227/orgsyn.045.0025.

Do you think the short-hand procedure would work? It is purely a guess from analyzing pcp synthesis. As such there is no formal literature procedure since this simplification is purely theoretical and does not actually exist.
 
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Yeah - saw that a couple of decades ago.

I guess anything is possible in theory.

Synthesis discussions is against BL user agreement.

It it's some obscure medicine then well maybe. But not 'how do I make this illegal drug'.
 
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I just noticed it while I was working on a page called 4-Chlorophenylacetonitrile. The other compound this precursor is used to make is the para-chloro analog of venlafaxine. Wy-45,881 is still the named analog though, which is the meta,para-dichloro analog and is the strongest analog in the series. Dan's synthesis of 4-(4-chlorophenyl)-4-(dimethylamino)cyclohexan-1-one [65618-71-5] looks far too difficult though. If my simplification suggestion works this would be a novel way of making the compound.
 
4DQSAR said:
I think it was a group of French researchers who took amphetamine and added a methyl side-chain to the benzylic (beta in old money) carbon. It turned out they were almost as active as amphetamine if resolved
Click to expand...
There's Vonedrine aka N,β-dimethyl-phenethylamine, a (mild?) NDRA. It's quite easy to make from the commercial aldehyde though.
pubchem.ncbi.nlm.nih.gov

Phenpromethamine

Phenpromethamine | C10H15N | CID 22276 - structure, chemical names, physical and chemical properties, classification, patents, literature, biological activities, safety/hazards/toxicity information, supplier lists, and more.
pubchem.ncbi.nlm.nih.gov pubchem.ncbi.nlm.nih.gov
 
Hey - I've just realized that I'm unaware of any examples of Dans work in which it wasn't so much 'because the science demands this', but because SOMEONE just kept asking.

Every so often we do come across some unexpectendly potent.

IF someone had a general synthesis for something like 4-[(6R,10bS)-1,2,3,5,6,10b-hexahydropyrrolo[2,1-a]isoquinolin-6-yl]aniline, that would provide for someone looking into these seemingly highly potent and yet syntheticall complex series is a unique problem.

IF I'm honest, I would first either obtain a sample of para ethnyl amphetamine or the para ethynyl homologue of mephedrone. On the basis that this is a good waypoint i.e. if the ethnyl mimics am MD ring (or more likely a methoxy).

Because, UNLESS you have PROOF that a compound is active in man, exactly what is someone supposed to have done. Lest we forget, animal models often do awful jobs.
 
The Straub Tail Reaction was supposed to detect opiate-like activity but famoustly one candidate just produced the same tail response.
 
I discovered from that Lenz opiate book you gave me the link to had the exact same idea as me only no citations were provided.

However it has been done at Grunenthal here in 2007:

[1] Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Stephan Wnendt, US7183436 (2007 to Gruenenthal Gmbh).
[2] Bernd Sundermann, Hagen-Heinrich Hennies, Werner Englberger, Babette-Yvonne Koegel, US7211694 (2007 to Gruenenthal Gmbh).

If you see the synthesis above it seems practically crazy of Danny to pave in that synthesis. I wonder why he paved it like that for.

Do you think it's because at the time he didn't know any better or was it one of his jokes?
 
Hyperforin produced by Hypericum perforatum (St John's wort). Potentially a triple reuptake inhibitor.

Screenshot-20260221-005152-Brave.jpg
 
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