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Topic: Acid Hydrolysis of Hexamine in the Delepine Reaction  (Read 5790 times)

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Offline macman104

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Acid Hydrolysis of Hexamine in the Delepine Reaction
« on: February 25, 2008, 12:23:30 AM »
I am working on the delepine reaction which is attached.  I know after hydrolysis with ethanolic hydrochloric acid, I will end up with the primary allylic amine and then the text says that I will generate NH4Cl and formaldehyde (which will be in the acetal form with ethanol).

I know the first step is an SN2 attack of the carbon and displacement of the bromide.  This generates our first tertiary nitrogen.  In searching for a mechanism, I found one for the reaction of phenol with hexamine (I believe it was to add a CH2 although I'm not sure).  The mechanism used for the phenol reaction is below, but applying that mechanism to my hydrolysis leaves me an issue at the end which I'm not sure how to resolve.

How do I go about removing the hexamine group and breaking it down into the formaldehyde and Ammounium chloride salt?

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