Install and run this AVCWare iPod to iTunes transfer software
First connect your iPod to your computer via USB cable. Then install and run AVCWare iPod to iTunes Transfer. After done, all information about your iPod, such as type, capacity, version, serial number, and format, will be shown on the main interface as below.
Select iPod music to remove into iTunes library
Open the library/playlist that you want to export files, and then check the file(s) you want to export in the file list. In this case, you should select music to remove into iTunes library.
Remove iPod music into iTunes library
Click the Add to iTunes button to start removing your iPod music to iTunes library.
Tip3: Before removing music from iPod to iTunes, please first check "Copy files to iTunes Music folder when add Music to Library" in iTunes advanced setting. Open your iTunes and follow the way: Edit - Preferences - Advanced - Copy files to iTunes Media folder when adding to library.
When you are finished, you can remove your iPod music to iTunes quickly. Below picture is the transfer progress.

A few seconds later, the transfer will be finished, click OK button. That' all!
Tip4: When this iPod to computer transfer is started, it will modify the automatic synchronization of music/video to manual synchronization between iPod and iTunes.
Related Guide:
How do I import songs from my iPod to iTunes
How to transfer music from iPod to new iTunes library
How to get my songs from iPod touch to another computer
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