Can imines be catalytically hydrogenated?

Can imines be catalytically hydrogenated? According to the DEA this appears to be possible. However I cannot find any other references to catalytic hydrogenation of imines anywhere else. 


![enter image description here](https://i.stack.imgur.com/2mIuZ.png)


<http://thedea.org/synthesis.html>




Yes, imines can be catalytically hydrogenated. Chapter 8 of Nishimura's *The Handbook of Heterogeneous Catalytic Hydrogenation for Organic Syntheses* is "Hydrogenation of Imines, Oximes, and Related Compounds" and gives several examples to work with.


The most analogous example in the chapter to your pictured reaction is Archer et al.'s preparation of 3α-(2-diethylaminoethyl)-aminotropane, wherein tropinone was condensed with N,N-diethylethylenediamine to give the imine, which was then catalytically hydrogenated at between room temperature and 50 °C over platinum oxide or Adams catalyst with 60-70% yield.


[Archer, et al. *J. Am. Chem. Soc.* **1957**, *79*, 4194](https://pubs.acs.org/doi/10.1021/ja01572a056)


 2

Several methods on the reduction of imines are outlined on [Wikipedia](http://en.wikipedia.org/wiki/Hydrogenation_of_carbon%E2%80%93nitrogen_double_bonds). Another method using catalytic hydrogenation is given [here](http://en.wikipedia.org/wiki/Imine#Imine_reductions).


 0