Is Converting a Secondary Amine to a Primary Amine Possible with This Route?

[kankerfist]

I numbered each reagent and product so you can point and laugh accurately. Any tips would be awesome!

 

[kankerfist]

I don't really need a full walkthrough, but if any you you guys spot a product/reagent 1-19 that you notice is right or wrong then please let me know :)

 

[GCT]

The route seems excessive, you won't get a significant yield with it, the significance here is converting a secondary amine to a primary amine, you should search for methods that have to do with this topic in general.

You're approach of creating the double bond seems to be a good initial step, the next one would be to induce the carbon nitrogen double bond since it is more favorable when its conjugated with the Benzene ring.