When I wanted to put music from an ipod into my itunes I found Music Rescue 4.0 to be very simple to use. With its itunes designed screen it is very familiar to work with. You can also play an ipod straight from this application but why would you want to do that when you can just copy those files into your itunes and play it through there.
Music Rescue 4.0 link
http://www.macupdate.com/info.php/id/7749/music-rescue
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