the move hypnosis
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hypnosys and snore in three turns also insomnia and vital spirit are abilitys that prevent sleep
There are a couple moves such as, sleep powder, grass whistle, sing, yawn, and one other move that I can't think of right now.
Yes Umbreon learns hypnosis I don't know when though. Get it to level 60 and go to the move toutor.
You can find it in the granite cave. It teleports straight away so use a move that either puts it to sleep or fake out. Hope this helped.
There are no items that can put Pokemon to sleep, only moves like hypnosis and sleep powder.