HT1351: iTunes: Syncing media content to iPodLearn about iTunes: Syncing media content to iPod
Currently Being ModeratedAug 10, 2012 5:16 PM (in response to pnay_lover)
You can't do it using iTunes, except for songs you purchased from the iTunes Store (and purchased songs can also be re-downloaded from the iTunes Store Purchased screen). However, there are third-party methods and utilities that will let your transfer song files from iPod to computer. If you do a Google search on something like "ipod transfer," you should get some links.
Once the song files are on your computer, you can add them to your iTunes library by dragging the files (or the folder containing the files) to the iTunes window.