Electra - 10-1-2014 at 14:22
Formaldehyde is known to be effective in methylating compounds when the subsequent molecule of the reaction is reduced through means of something such
as Zinc in an HCL solution or other reducing solution. http://www.sciencedirect.com/science/article/pii/S0040403907...
This process has been known to be applicable to a very large range of alpha amino acids, numerous amines, and many other compounds.
My question is, what is the compound that results when formaldehyde is reacted with, for example, the amino acid Piperidine. In the above paper
Piperidine is reacted in high yields with Formaldehyde and then reduced with zinc in an acidic solution to form N-MethylPiperidine.
My question is what is the molecule immediately following the reaction between Piperidine and Formaldehyde? What is the reaction that takes place? How
is formaldehyde modifying such a molecule, and additionally what byproducts are formed by such a reaction? I'm trying to form a clear picture in my
head of the resulting molecule before reduction, but really have no idea what's going on in this reaction. Does anyone know?
Random - 10-1-2014 at 16:27
Does this also work on phenols?
Electra - 10-1-2014 at 17:34
Good question. The technique is formally known as reductive methylation so going from there might be a good start. I'm no chemistry genius but there
are a lot of yet to be tried reactions that likely have a fair bit of potential for positive results.
leu - 10-1-2014 at 18:49
There's probably scores of threads on this web site in which this subject is discussed that could be easily found using:
http://www.sciencemadness.org/talk/search.php?fid=10
and of course there's the multilingual internet encyclopedia:
http://en.wikipedia.org/wiki/Hydrogenation_of_carbon-nitroge...
and
http://en.wikipedia.org/wiki/Imine
that answers this query as well 
The end results from the effort applied 