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By the time I left my apartment, my friend was still there, so he might have taken it.

When I left the apartment, my friend was still there, so he might have taken it.

I know what 2nd expression means, but not so sure about the first expression. Does it convey the same meaning as the 2nd expression?

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The first expression does not quite work. You could say:

At the time I left my apartment, my friend was still there, so he might have taken it.

this is because we are using our knowledge of the friend's location at a particular time, that at which we left the apartment.

We use the term

By the time

to talk about events occurring in a period up to a certain time

By the time I woke up my friend had already left

or in the famous song

By the time I get to Phoenix she'll be rising ...

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