What file format is your video files? you must keep them in mp4, mov, m4v format that itunes reads.
Then drop them into iTunes and sync with your iPad.
If you are looking for a video file converter to make your movie files available for iTunes, i recommend you use AppGeeker.
Click to check the possible solution > http://www.ilikemall.com/how-to/convert-flv-to-mp4-mac.html
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