Can't upload iPod Classic contents onto a new computer

The PC that I had paired with my iPod Classic died. I can't figure out how to upload the iPod's contents onto a new computer. Is this possible?
I also put a new CD on my Mac that won't sync with the iPod Classic.
What am I doing wrong?

I think the problem could lie with the sharing of the iTunes account. In itunes on your computer, under "Store", click "Authorize this computer" and login it using your brothers itunes account. Now try syncing the Ipod again and doing a FACTORY RESTORE of it

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I had this issue recently, due to changing HD for an SSD.
In my case, since the library in my iPod was synced to the HD it was not syncing to the library in the SSD, though they were the same (had the same contents).
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Thanks for visiting Apple Support Communities.
See this article for the options to transfer music from an iPod to a computer:
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http://support.apple.com/kb/HT1209
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Download your media through iTunes Match2.
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Can't upload iPod Classic contents onto a new computer

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