Re: ORGLIST - orglist Digest - V01 #193

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From: Arthur Cammers (cammers$##$caribe.chem.uky.edu)
Date: Fri Oct 02 1998 - 14:16:25 EDT


On Fri, 2 Oct 1998, Richard Prankerd wrote:

> >Dear pals,
> >Could any one suggest me why the following reaction does not work.
> >1. I have reacted piperazine (2 mole) with n-propyl bromide (1 mole) to
> >give n-propyl piperazine. The reaction was carried out in ethanol (under
> >reflux)with 1 mole of NaOH for 7 hrs. Unfortunately, what i obtained
> >was the disubstituted product and unreacted piperazine.
> >
> >I could be much greatly if you'll could offer me other procedure to
> >synthesize the above mentioned compound. I would also like to know on
> >the commercial availability of theis compound. Any other suggestion is
> >welcome.
> Unfortunately, this is a classic problem -- how to react only one of two
> functional groups which have similar or the same reactivity. I've had to
> deal with a similar type of nucleophilic substitution problem and found
> that a mixture of monosubstituted and disubstituted was always obtained, so
> a chromatographic separation was essential. It appears in your case that

Dear Roshan Deen:
1) Reductively couple propanal with 1-piperazinecaboxaldehyde
(commercial).
2) Hydrolyze the formyl group.

Arthur Cammers-Goodwin
U. Kentucky

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