May 21, 2022, 06:36:26 PM
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Topic: Reductive amination of aldehyde and secondary amine  (Read 353 times)

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Offline Seanlet

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Reductive amination of aldehyde and secondary amine
« on: June 23, 2021, 07:05:27 AM »
    By dent of the precursors we are able to obtain. One precursor has a secondary amine moiety while the other has an aldehyde moiety. I have seen various mentions of the 2 reacting to form an enamine which produces an carbinolamines which dehydrates to a enamine.

 I have found several references but in all cases, yield is low. Ideally I would protect the other functional groups (phenol, allylic alcohol, tertiary alcohol) and add an acid chloride and reduce the thing but all of those protections and deprotections make it rather unwieldly.

 Can anyone give me a reference to a higher yielding secondary amine + aldehyde synthesis.

 I should add that the BP of all of the reagents is above 100°C so removing the water is not difficult. I apologise if this has been asked before but I did hunt the site for a similar reaction and didn't find one.

 I should add that the amine it part of a piperidine ring while the aldehyde simply provides a pendant aromatic.

As I mentioned, I do have a second route but thiis means 10 steps rather than one and so presuming that all yields <100% then this simple route might work out the most efficient.

But I'm sure that the experts will know better than I. With thanks.,

Offline rolnor

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Re: Reductive amination of aldehyde and secondary amine
« Reply #1 on: June 23, 2021, 08:18:52 AM »
Is it an aromatic aldehyde? Can you give the structure?

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