How do you add songs from iTunes 11 that is not the main synced library to an old 80GB classic iPod?

My boyfriend and I found his old 80GB iPod classic in his stuff. I synced it to my Macbook Pro. I was then trying to sync all his music from his iMac onto the iPod so that the iPod contained both libraries, but in the iTunes 11 I cannot manually drag and drop all the music onto the iPod. I could've with the other devices on the computer but not the iPod Classic. Is it just too old? How can I put all our music onto this one iPod?

See this older post from another forum member Zevoneer covering the different methods and software available to assist you with the task of copying content from your iPod back to your PC and into iTunes.
https://discussions.apple.com/thread/2452022?start=0&tstart=0
B-rock

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