ITunes :: Copy A Recording In (Mac) To IPhone?

My friend recorded a lecture using a microphone attached to his old-model iPod nano. I told him it would be easy to transfer to his computer, a Macbook Air. It was; he attached via USB cable, iTunes detected new voice memos, he said yes please copy the voice memos, and they were copied. Yes! He can now listen to the lecture on his MB Air. But... Now he wants me to listen to the lecture as I drive around with my iPhone 4. I thought this would be easy: attach my iPhone to his Air, open iTunes, and tell iTunes to put the lecture on my iPhone. But... It won't copy! When I try to drag the lecture from the main list in iTunes onto my iPhone in the source list, it always snaps back. There is no error message; it just "won't go". There are no copyright issues; it's a recording he made himself from a college lecture. 

I thought maybe the issue was that the file was in WAV format. (I don't know if this is always the case, or if that was the format used natively for Voice Memos on his old-model iPod Nano.) I told iTunes to create an AAC version, which it promptly did. But that, too, will not drag-and-drop onto my iPhone. There are zillions of programs to copy from an iPhone or iPod onto a Mac, but how do I go the other way?

Info:
iPhone 4, iOS 5.1