stuck compound?

[somae]

I've been trying to separate a secondary amine using silica gel (230-400 mesh). The compound seems to be stuck and won't elute. I've used 100% methanol and thf. I started with about 6-7 grams of product and have only gotten back about 1 gram total.

The silica fluoresces under uv which would seem to mean that the product is still there.

Any help appreciated.

[Uwe Neue]

You can try to elute with water/methanol. If this does not work, you may need to add a buffer or an acid.

[ym3142]

one way is adding Et3N in the MP;
or you may have to avoid Silica and use alumina.
or other LC such as size exclusion or ion exchange,