The safe operation of high pressure pipe line systems is of significant importance. Leaks due to faulty operation from the pipelines can lead to considerable product losses and to exposure of community to dangerous gases. There are several leak detection methods of pipeline network which have recently been suggested. The negative pressure wave detection technology, which has advantages of short time detection availability, accurate leaking location estimate capability and cost effective, is concentrated in this study. Theoretical analysis of the flow characteristics for leaking through a hole on the pipe wall has been performed by using Fluent 6.3, commercial CFD package. The results of 3-dimensional analysis near leaking hole confirm the occurrence of negative pressure wave, and the results of 2-dimensional analysis verify the characteristics of propagation of the wave which travels with speed equal to the speed of sound in the pipeline contents. Characteristics of leakage and pressure in a pipe with a hole have been analyzed for the various pipe and hole sizes.