I perform reaction between compound 1 (liberates HCl upon hydrolysis) and in situ synthesized imine compound 2 at 65 centigrade
The hydrolysis step is essential for CPD1 to work, but the liberated HCl in the aqueous media hydrolyze the imine CPD2
How to do capture HCl from the media to protect the imine from hydrolysis whereas the reaction is one pot reaction, i.e., all materials are charged together in the same vial?
Compound 1 (liberates HCl) + Compound 2 (in situ amine + aldehyde, imine) = Product
When HCl is liberated as a gas in a reaction, it is either flushed out from the system by a continuous stream of nitrogen or by using a mild base as HCl scavenger (such as pyridine or triethylamine).
However, you may need to use glacial acetic acid in the reaction that forms the imine taking into account the possibility of a small side reaction with the primary amine which does not ruin the final result. Best wishes for success in your research.
Depending on the amount of the HCl produced, buffer may not work as much. I think the best thing to do is to monitor the reaction to determine the time for the liberation of the HCl. When that is achieved, then an equimolar amount of a base (NaOH or bicarbonate) can be added to the reaction mixture at that point in time during the reaction to neutralize the acid...
Nizar Matar Thanks a lot, pyridine works very fine
Jude Ayogu thanks a lot, i tried inorganic base but not working very well with my reaction mixture
For imine formation you need a buffered media, because you need some acid to activate the carbonyl and allow it to react with the nucleophilic amine, however too much acid will protonate all the amine, and there went your nucleophile.
When mineral acid, like HCl, is produced, the best is to have some non-nucleophilic base present, usually a tertiary amine. Pyridine or TEA can be used, for instance, whenever possible.
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