ORGLIST: hydrochloride salts

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From: David L. Price (price$##$mail.chem.sc.edu)
Date: Wed Dec 22 1999 - 12:39:08 EST


Dear Group,

This question may be too basic for the list, but here it is. I've just
isolated a polycyclic amine from a preparative RP-HPLC run which used
0.1% heptafluorobutyric acid (HFBA) as the aqueous buffer and
acetonitrile as the eluting organic buffer. After drying the pooled
fractions, I assume that I have the HFBA salt of the protonated amine.
To obtain the hydrochloride salt, would I just dissolve the product in
dilute HCl, then lyophilize? My reasoning is that the pKa of HCl is
lower than HFBA. Adding the HCl would protonate the HFBA which is quite

volatile in the acid form. If this is correct, then can one assume that

any amine that is prepared / sold as its hydrochloride salt is stable in

HCl?

Happy Holidays,

David L. Price
price$##$mail.chem.sc.edu

Department of Chemistry & Biochemistry
University of South Carolina



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