Hi,
I'm currently dealing with amine synthesis and since I'm new on this field I also don't have much experience on the purification. Here's my problem:
I tried an unusual method to convert a benzylic nitrile to the corresponding amine. It involves DIBAL-H, NH4Br and NaCNBH3. I can't use LiAlH4 or H2 to reduce the nitrile as it would mess up other functionalities in the molecule.
After acid base extraction the TLC (silica, EE/MeOH, 10:1, 5% TEA) of the crude product showed several spots whereas only one of them was blue/purple (ninhydrin). The other ones were somewhat brown or yellow... After column chromatography (same system as above) I was able to isolate all spots I saw on the TLC plate except for one: the blue amine spot, which I think is my desired product.
So does anyone know what's going on? Hope you can help me...
Besides: Rf value of the blue spot was ~0.35 and there were two spots below that one which I isolated as well. And I didn't pretreat the silica with TEA...
