This is after Shift+F9:
F9 runs fine.
When I remove “–” on the end, runs fine as well Shift+F9
Shift+F9 uses blank line (or start/end of edit buffer) as statement terminator. The text in your screenshot is sent in entirety to Oracle resulting in the error. You either need to use F9 or follow the rules of Shift+F9 by moving the comment down to line 3 or greater.