Sync music with 2 different apple accounts fails

Hello,
I have got two different Apple ID's, one in the German iTunes Store and one in the Spanish iTunes store. The Spanish ID I mostly use for icloud but sometimes to purchase Apps or other Media in Spanish but I usually use the German iTunes ID... so far without problems.
A week ago I downloaded some music by accident with the Spanish ID and tried to sync them to my iPhone or iPad mini (on which I have got many songs purchased via the German ID). I tried to push the new songs manually in different way's but without success... I also tried to change the ID on my iPhone or even in iTunes (Mac) but cannot get them moved. Strange is, that when I have my iPhone connected to iTunes, I can see in front those songs a ring with interrupted lines..
Does anyone has an idea? Many thanks in advance
BR
Christian
Using MacBook Pro with OS X 10.9; iPhone 4 and iPad mini with iOS 7.0.4 and iTunes 11.1.3

If you are using different iTunes Store accounts on the same Windows or Mac OS X user account and haven't explicitly set up a separate library, there will only be one iTunes library regardless of how many iTunes Store accounts you have. iTunes libraries are completely separate from iTunes Store accounts.
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