iPod Classic 6th Gen not syncing with iTunes 11?

I got in the car tonight to find my iPod requesting to be restored. So I went home and plugged it in and restored it to factory settings as I was told. Now when I try to put my music back on, it simply doesn't go. Nothing crashes, no problems occur, it just doesn't happen. It says for a split second that it's syncing, but then that goes away and I still have a blank iPod. I've now restored it four times to no avail. What is going on and how do I fix this?!