FR 5322 then FR 3614 at Madrid
Milan → Madrid → Prague
Timetable, Madrid time
19:45FR 5322 from Milan at the gate
18:45FR 3614 to Prague leaves the gate
23 h apart on the timetable, overnight
FR 3614 leaves 23 h after FR 5322 arrives on the timetable: more than half a day, so not a connection we count.