Help please - iTunes classic won't synchronise - Errort message '-69'

Hi.  I have a classic 1st generation iPod (60GB) and every time I try to download my music collection from iTunes it fails after a short while and gives me an error message (-69) and says that the synchronisation failed.  I've reset factory setings about 20 times and do have the latest version of iTunes.  Any advice gratefully received.  Thanks.

Hello dmbnewfie,
Welcome to the Apple Support Communities!
I understand that your iPod classic is not being recognized in iTunes when you connect it to your computer. I know you have tried some troubleshooting on the Apple website as well, but without knowing which steps you have completed, I would suggest working through the attached iPod classic Troubleshooting Assistant. 
Apple - Support - iPod - iPod classic Troubleshooting Assistant
Have a great day,
Joe

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