Hi, I used the free version of iPod 2 mac (which works also for my iPhone).
http://www.macroplant.com/podtomac/
You can either purchase it for 20 bucks and have cool stuff.
or you can use the free version where you have to do it one by one.
However, I have 1,300 + songs and once I started I got it over in like an hour maybe (use your keyboard down arrow + click, much faster).
Also it will say you have to wait for 60 seconds after transferring x number of songs, but if you ignore the message after the 60 seconds are down, it will just allow to transfer unlimited.
So I am very happy of this program, now I have all my songs on my mac and itunes library (which I will back up right away so I don't have to do it agaiN!! lol).
Good luck !