Draw a longitudinal profile of the pipeline.
Draw the hydraulic grade line (HGL) from the delivery pressure of the pump, down to the pipe outlet. The HGL must be a straight line to the outlet because there is no head at the end - it is at atmospheric pressure.
If the HGL is more than about 9 or 10 m below the pipe, column separation will occur. At the column separation, the pressure is about full vacuum (about -10 m of water) less the vapour pressure of the water (about 200 mm of water, absolute).
If the HGL is less than (say) 8 or 9 m of water, the system will operate like a syphon.
Positioning an air valve on top of the hill (so that you don't get an air lock on pump start up), will break the water column THEN the down stream pipe can become an open channel. For a quick check try Manning formula for Q = pump flow (based on the pump HQ curve & pipe characteristic curve) & see if the pipe can take the flow as an open channel. I usually check a full pipe first, then if the pump flow is less, the depth of flow can be calculated from the curves of flow vs depth (such as in AS 2200).
Summary
HGL above the hill - pipe flows full.
HGL down to 9 m below the pipe - pipe flows full (as a syphon).
HGL 10 m or more below the pipe - pipe flows full on the upstream side & can be full or as an open channel on the downstream side, depending on the flow, diameter & pipe grade.
Barry Eng