ORGLIST: Di(2-picolyl)amine derivatives

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From: S. Woodman (chm4sdw$##$leeds.ac.uk)
Date: Fri Feb 01 2008 - 10:48:53 EST


Dear all,
I am trying to make the hydrochloride salts of several di(2-picolyl)amine
derivatives containing a -CH2-C(=CH2)-Ph group on the amine nitrogen. I have
added an excess of a methanol solution of hydrogen chloride, and attempted to
crystallise the salt by adding ether. While this does cause particulate matter
to form, said matter is impossible to filter, as it bonds to the filter paper
and can only be removed by re-dissolving it methanol. Furthermore, when I
remove the solvent in vacuo, I am left with an orange oil identical to the
starting materials. What am I doing wrong?

Many thanks,

Sam Woodman.

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