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To transfer iPhone-purchased songs and books to iTunes and computer, i often use iMacsoft iPhone to PC Transfer, it can easily backup purchased songs, books and downloaded podcasts and iTunes U in an easy way.
If you have music backups of the old iPod in iTunes, you can easily sync the songs with the new iPod. If you don't have backups, you are also able to transfer purchased songs from the old iPod to iTunes using the "Transfer Purchases" function of iTunes. You won't be allowed to transfer the songs from the old iPod to computer or new iPod if the songs are not from iTunes. This is how to transfer music from old iPod to new iPod with the "Transfer Purchases" function of iTunes: Step 1. Plug the Old iPod into computer via the USB cable. Then launch iTunes. Step 2. Click "File > Device > Transfer Purchases". iTunes will automatically transfer the songs to iTunes library. Step 3. Plug the new iPod into computer. Then import the songs from iTunes to the new iPod.
You can use a program called Copy Trans Manager to import your songs from your iTouch back into your computer. You can use a program called iDump for all your other Apple products. See related links below for links to these programs.
You can download on the itunes icon on you ipod or you can connect to computer and then put in a cd. You can then transfer the songs. It is legal.
plug your ipod to the computer, open itunes, select Music and manually transfer the song to the ipod