Solvents For Prodines..

[Bwiti]

Lets say you have a reaction mixture, and you want to extract 1-methyl-4-phenyl-4-acetoxypiperidine or similar compound out of it. I know that benzene can be used. In

https://www.thevespiary.org/rhodium/Rhodium/pdf/prodine.pdf

, Epikur says that toluene can be used instead, but I remember someone telling me that the product could react with the toluene, creating a toxic bi-product. Is this true? What solvents can be safely used? Thanks!

[Rhodium]

I find it highly unlikely that toluene would react with anything in that soup if benzene doesn't.

It is however technically possible that toluene is activated enough to undergo friedel-crafts acylation with the propionic anhydride catalyzed by the H₃PO₄, while benzene isn't enough activated for that to happen, but if that reaction pathway is possible, then why isn't the styrene or the product FC-acylated? In any case, if any such byproducts would be created, they would be removed by the distillation of the freebase and the subsequent recrystallization of the hydrochloride salt of the product.

[pHarmacist]

A distant friend has made a solid batch of prodine in a country where drugs including prodine are legal and reported that he used toluene without any problems. SWIM followed the same procedure as presented in the patent supplied by Epikur.

[Bwiti]

"Who said that, where and when?"

  Sorry, but I don't have a clue

"It is however technically possible that toluene is activated enough to undergo friedel-crafts acylation with the propionic anhydride catalyzed by the H3PO4"

  There would be no anhydrides present, because dH2O would be added first.
  Thanks for clearing that up.. I'm guessing that means that heptane, xylene, etc. can be used also, so that's cool as far as money goes.