Hello, i am in my second year at university, studying chemistry. In this year's laboratory, our professor told us that we should make a compound of his choice. He would not help us at all saying that we learned enough the past year in order to pass this course(he would only let us start the experiments if we show him a good synthesis plan for the compound he gave us). So i found some steps that seem to be fine at reaxys and the professor told me its okay to start. At my last step i need to do a reductive methylation and add 2 methyl groups on an amine. I will use formaldehyde, the amine will react with a schiff base reaction and i will get an imine. Then i use Sodium cyano borohydrate to reduce the imine. And repeat again to get 2 methyl groups on the amine. Now the problem is that the cyano group of sodium cyanoborohydrade reacts as a nucleophile and i might get the byproduct (NC-N-CH3) in a high %. I want to use column chromatography and separate the cyano byproduct and the desired product. I think the compound with the cyano group is polar enough to be separated from the disubstituted amine but i cant find in the literature any particular information about the separation of cyano byproducts with column chromatography.
Note: The desired molecule is non-polar and the byproduct has a cyano group that i think it might be possible to be separated with column chromatography. The amount of sodium cyano borohydrate is in the scale of mmoles , so there is no big danger of the produced gas HCN.
