ORGLIST: synthesis of 3-chloroprocainamide (declopramide)

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From: Eugene Leitl (eugene.leitl$##$lrz.uni-muenchen.de)
Date: Tue Jul 25 2000 - 18:19:47 EDT


Hi,

I'm trying to make about 30 g of 3-chloroprocainamide (declopramide),
which (I presume) looks thusly:



3-chloroprocainamide (?)

The only literature ref I've found (not yet in my hands) so far is

       Hua J, Pero RW 1999. Pharmacokinetics and central nervous system
       toxicity of declopramide (3-chloroprocainamide) in rats and mice.
       Anti Cancer Drugs, 10:79-8

In case anyone knows a handy literature ref for synthesis of either
abovementioned, or metaclopramide (very much the same thing, only with
an extra methoxy group) I would very much appreciate that.

I was thinking about making 3-chloro, 4-amino benzoyl chloride with a
protected amino group (which protective group would you suggest? I
obviously can't use an amide, since it's present in the target
molecule), and let it react with assymetrical N,N-diethylethyldiamine
(which I presume is commercially obtainable), in pyridine or
triethylamine.

Do you see any failures with such a scheme? Any alternative
suggestions?

Thank you very much.

-- Eugene
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