If you have not done so already, you can download TouchCopy from here.
TouchCopy enables you to transfer all your songs and playlists to iTunes in just a few mouse clicks. To transfer all your iPod songs into iTunes click on Music from the list on the left in TouchCopy and then click on the "Copy to iTunes" button. You can also choose individual songs or groups of songs you wish to copy by Shift-Clicking songs in TouchCopy.
To transfer your iPod playlists into iTunes select the Playlists you want from the source list in TouchCopy. You can select multiple playlists by CTRL-Clicking items in this list. Once you have selected your Playlists - click the "Copy to iTunes" button in TouchCopy.
When transferring a playlist into iTunes, the songs are transferred and a new playlist of the same name is created. Note that if a track is already in your iTunes main Library, TouchCopy will not create a duplicate of that track in iTunes, it will just add the track to the Playlist.
If you continue to have problems with transferring music and playlists directly to iTunes, please try copying music to your hard drive by clicking on the Copy to PC button in TouchCopy. You can then importing your music into iTunes by selecting the File tab and then Add folder to library in iTunes.
If you copy your playlists to your hard drive, TouchCopy will produce an XML file named after the Playlist you are copying. This XML file contains information about the tracks and track order of the Playlist. The XML file can be used to import the playlist into iTunes. To import the playlist into iTunes, in iTunes, select 'File -> Library->Import Playlist...'. Select the XML file saved by TouchCopy with the same name as the playlist you require and click 'Open'.