Dr_Heckyll; As you can see, the first three of your amphetamine derivatives are the ones I am trying to synthesise! Do you have any experience/references for these compounds?
Nemo_Tenetur; I'm sure you know almost every amphetamine derivative imaginable is scheduled in the UK
. This synthesis is a legitamate way to test whether I can do such a condensation, and the activity of the final compound is not the main concern (although it would be fantastic if it was active!). I'm still waiting for my 2-trifluoromethylbenzaldehyde to arrive...
Rhodium; Yes, I have thought of the problem of the basic nitrogen interfering in the Knoevenagel condensation, but was hoping that because;
a) an aromatic amine is less basic than an aliphatic one (cyclohexylamine in this case), and
b) the tertiary amine in the pyridine ring cannot be deprotonated, therefore cannot react with the aldehyde as such,
it would not interfere in the condensation. Of course something may have gone wrong, because I don't have crystals. However, I may have the correct product, as I don't know of anyone else synthesising 1-(4-pyridinyl)-2-nitropropene, and it's melting point may be well below room temperature.
Also (please forgive my ignorance), what is the structure of alpha-pyrrolidinopropiophenone? Is it just propiophenone with pyrrolidine bound via the nitrogen to the alpha carbon (the same place the nitrogen is bound in all PEA's)?
And finally, can anyone think of a reason why forming pyridine-2-propanone wouldn't work via Barium's new method, in
Post 333551
(Barium: "benzaldehydes to phenylacetones", Novel Discourse)? I would love to get this to work somehow!
