I am performing Alkyne Zipper Reaction which requires 1,3-Propanediamine as a solvent. After completion of reaction, I need to extract my compound which is highly polar. But, since 1,3-Propanediamine is highly polar too, it extracts out with the product.
Please suggest some methods to get rid of 1,3 Propanediamine.
what is the boiling point of your product?? if the boiling point is high then you can evaporate the solvent under vacuum. good luck.
Then try to wash with dil. HCl to get rid off 1,3-propanediamine. But check that, what will be the effect of acid on your product. Also check the attached paper, probably it will be useful for you.
Thank You Avtar.
I washed with dilute HCl but I observe that some alkyne converted to Alkene.
This is a big hindrance for me now.
Try using a copper sulfate in water instead of acid. Sometimes it works better...
Thank you so much Prof. Marcelo. I will try this method and get back to you.
I often used hexamethylphosphoramide (HMPA) as a cosolvent in synthesis reactions. Our standard procedure for removing this material from the reaction mixture on workup was to extract with a half-saturated solution of copper sulphate until no precipitate of copper (II)-HMPA complex could be observed. It was completely effective at removing HMPA, and I imagine it would work equally well with 1,3-propanediamine. Of course, your desired product must not be able to complex with the copper ion and so be removed at the same time.
Another posibility is to wash your mixture with CuSO4 solution: For 5 mL of an amine solvent, use 5 X 10 mL of 10% aq. CuSO4 solution during the aqueous wash. This should remove all of the amine. I hope it works for you.
You could try using Cu(ClO4)2 or other Copper(II) or Ni salt to complex out the 1,3-diaminopropane.
Thank you so much Prof. Simon, Richard and Arnab. This is really helpful.
http://www.waters.com/waters/en_AU/Sep-Pak-SPE/nav.htm?cid=513158&locale=en_AU
you can try these sep-pak column or use reverse phase silica for column chematography and elute with water and ACN
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