How to connect and sync music from windows music player to a smaller ipod classic

I've been trying to put music onto a smaller version of a ipod classic 5G, which can only have 2GB of data. Somehow i cannot connect the device and it won't let me sync the music. I've connected other devices to Windows Media Player and it worked, but this does not. Please tell me if you know how to resolve this problem, i will appreciate it.