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This may be a bit off-target, but if understanding your procedure imagine that it COULD work.
Understanding is that you currently have your HTC set to dial into the PBX system - your steps 1 - 3 - until reaching the point where the system needs the dial-out number you wish to use.
At this point, your HTC dialing procedure halts and you manually select the Contact you wish to dial, but (alas!) the HTC considers this as a NEW call, so it puts the initial call (into the pbx system) on hold, and thus the pbx box never receives the number you want it to dial.
An alternative approach might be to select the Contact FIRST, and to simply prefix his / her phone number with your steps 1 - 3. Now the Contact Phone Number is simply part of the same long stream being passed to the pbx system, so there should (hopefully!) be no need for the HTC to consider it a new call.
IF this alternative would work, you could presumably batch update all of the appropriate Contact records, into a newly defined Phone Number field, and create & assign a new Category to help select them....
Good Luck!
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