Help with theoretical synthesis step

[Orgman]

Good day all.

 

3,4-dichloro-N-(2-hydroxycyclohexyl)-N-methylbenzamide --> 3,4-dichloro-N-(2-(dimethylamino)cyclohexyl)-N-methylbenzamide

 

These two are fairly similar with the exception of (2-hydroxycyclohexyl) and (2-(dimethylamino)cyclohexyl) respectively.

 

Would it be safe to assume there would only be one or two steps to get from one to the other as shown at the top of tbis post?

 

Also as I am fairly curious, imagine these two were mixed together 50%/50%. How would one go about separating the two?

 

Thanks in advance