I cannot get music from my library to my ipod classic.  It syncs but not transferring music

I bought a  new laptop and authorized my new computer to share my laptop.  I have a bunch of music in mu library that is not transferring to my ipod classic.  The ipod will sync but not everything is transferring.  So frustrating.  I am trying to copy and paste, not working.  I am selecting song and select "add to Phone" and that is not working.  How can I move these items

Or how do I change the 5 devices. Some are not used anymore

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