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What is a chemical reason why the yield of  4-((benzylamino)methyl)-2-methoxyphenol from P-vanilin and benzylamine via reductive amination...

What is a chemical reason why the yield of  4-((benzylamino)methyl)-2-methoxyphenol from P-vanilin and benzylamine via reductive amination with NaBH4 is below 100%? Also in this reaction why would the crude of the imine be less than the purified imine, the imine is (E)-4-((benzylimino)methyl)-2-methoxyphenol.

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Answer #1

NaBH4 is good reducing agent in reductive amination.but not as much efficient.

First step will be nucleophilic addition of P-vanilin or benzylamine to the carbonyl group

It will covert into C=O to C=N

Mechanism of imine formation is diffrent.Possibility of dealkylation is more so NABH4 will be involved in the reductive amination to get E)-4-((benzylimino)methyl)-2-methoxyphenol..

There are two amines will be formed

primary and secondary

During the reaction various intermediate compounds will be obatined like enamines that why it is below 100% and purity also less than crude.

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