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Nzayisenga Emmanuel

Separation of secondary and tertiary amines

Brian Asbury  Follow
TLC with EtOAc 1-10% TEA can separate this type of compounds, run flash.

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Chaw Tin Zar Maung  Follow
Quote from:
In my experience, there is one trick you can try to separate secondary and tertiary amines chemically, using reductive amination.

This trick will not only add chromophore to secondary amine, but also reduce the polarity of the molecule significantly. Both of them will help the seperation in column chromatography.

Since you have the problem solved, you may save this trick for next time.

Well, thank you for the trick! But, as I mentioned in the post, I am preparing ligands for metals. I would save it for other topics.

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Antonio Daniels  Follow
In my experience, there is one trick you can try to separate secondary and tertiary amines chemically, using reductive amination.

This trick will not only add chromophore to secondary amine, but also reduce the polarity of the molecule significantly. Both of them will help the seperation in column chromatography.

Since you have the problem solved, you may save this trick for next time.

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Military Aircraft  Follow
Thank you for the replies :)
But, I figured out that N-Methylpiperazine has bp of 110~120 C, so I just dried it in the vacuum.
And, as you stated to separate in basic condition, I had another trial with more base. It worked really well.

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David Mott  Follow
I would first try to recrystallize it, but this is a sometimes intractable problem. It's better to run reactions that minimize the amount of undesired amine via the setup and reagents.

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Abdulalah T. Mohammed  Follow
Ah, I figured column wasn't an option from the way OP phrased it. Yes, definitely a column with triethylamine is the first option.

Another option, is it low weight enough for one or both to be fractionally distilled? Even easier than a column.

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