Compounds With the Most Frustrating Syntheses

[Smyth2]

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].

1,4-Cyclohexanedione monoethylene acetal

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.

 

[4DQSAR]

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'.

 

[Smyth2]

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.