Well now, we're getting to the nitty gritty of this. The amine will be more basic than the just formed amide. There will be a proton transfer. You probably need two equivalents of the amine as one will become tied up as the HCl salt, but I digress. The nitrogen will have one hydrogen and one lone pair. Now, whether you use the lone pair to add or you write the addition as acid catalyzed, you'll have to decide.