Thanks to all. But the spots of remaining ketone and imine is so close and of very high Rf that they could not be seperated. I will be even more interested if there is any chemical methods or some physical extractions etc.
Amines can be removed with acidic work up (0.1 M HCl) or using 10% CuSO4 solution. May have to extract few times to get everything in the aqueous phase.
Some metal-Schiff-base complexes are reversible and can be made by one-pot synthesis. In fact, I miserably failed in making some difficult to make Schiff-bases, but was successful in making their Fe and Ni complexes directly by one-pot synthesis. Such complexes readily separate out from the reaction mixture as pure compound. You may try this out in your case. You have to find out a suitable metal and then a method to get the Schiff-base back from the complex.
thanks to all....But Praveen in my case amine is not problem as it has considerable Rf difference. But do you have some idea how to remove acetophenone? Because it is causing the main problem.
Prof. Chowdhury, there are two ways to try to overpass this problem.
1) Use stoichiometric amounts for the starting materials in your transformation and try to displace equilibrium to the right with the employment of Dean-Stark trap and reflux of the reacting mixture at least for 8-12 h. In this way the remains of starting substances should be minor since the removal of water from the reacting bowl has been displaced through pseudoazeotropic conditions with the solvent trap. Also use absolute EtOH, MeOH or CH3CN solvents, since the formation of water is the side product in these reactions, and these type of solvents are willing to be hydrated in the reaction, this effect also displaces the reaction to the right side.
2) In the second option, I guess that you should employ recrystallization or phase change precipitation of your final mixture, since the iminic product, normally is of higher polarity than their corresponding starting materials. In this way it is possible to employ solubilization of the mixture with ethylacetate, THF or CH3CN, and then slowly add hexanes to promote phase change of the most polar product. In this way it is possible to separate or enrich one of the desired products without chromatography and so on. I have employed this procedure since 20 years ago and provided me pure enough products to be characterized throughly, even with elemental analysis and hig res. mass spectrometry.
Best regards and good luck with your experimentation. Hiram
Many of the above suggestions are good. Hiram's suggestion of driving the reaction by removing water is good. If starting materials are still present, you can always try using scavenger resins to fish them out. In your case, a primary amine resin and an aldehyde resin will be needed to remove your excess ketone and amine, respectively. The following link is for a vendor (I'm not affiliated with the company) that is a supplier of scavenger resins. Their website describes which functional groups of a mixture can be removed by using each resin.