I tried to deprotonate the methyl group of the picolinium salt, in order to attack the C=O belonging to the aromatic aldehyde. However the majoritary compound obtained is the condensation between the piperidine that I used as catalyst and the aldehyde. Conditions are:
EtOH, 80ºC, 1 to 18h and piperidine (0.5 eq)
I must say that the picolinium salt is bearing on the other side, an alkyl chain with a bromine in its extremity...
Thanks in advance
Does it need to be secondary amine? Because that is probably reacting with aldehyde to give enamine. Can you use a tertiary amine?
I do not think so, and yes, that's one of the secondary products, the other one is the piperidine replacing the bromine borne by the picolinium salt. I am searching for alternative to piperidine and pyrrolidine....maybe copper as I read recently
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