Do you use a Mac or Windows PC? If Windows, what version?
"A1285" comes up as 4th gen; is that correct? This document shows the iPod nano models
Identify your iPod model - Apple Support
As a test, shut down (power off) your computer and disconnect all USB devices. You can leave standard USB keyboard/mouse connected, if used. If your computer is a laptop, connect its power adapter so that it's not running on battery power. Do this to Reset (restart) the iPod
Learn how to reset your iPod - Apple Support
Start up computer, run iTunes, and connect iPod to a direct USB port on the computer, by itself. Is there any difference?