Cant figure out how to put songs on Nano!

Just got this nano, and im somewhat familiar with Itunes.. i JUST donwloaded the latest version, and ive made a new playlist and ive got all the songs i want on my ipod on that playlist.. i try to click update, but my ipod already says do not disconnect and the update ipod is not able to click under the file part.. what do i do? its been hooked up about 45 minutes and im only trying to add 17 songs.. please help

I think my Itunes doesnt recognize the ipod, i havent restarted since i downloaded this software so is that a good idea to?..
on the other hand, it might recognize the ipod because earlier it automatically downloaded the songs onto it that came with the Itunes.. then i deleted all my previous songs along with the ones that came with it.. now it w*ont let me load songs at all, and i have my playlist ready so.. please help

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