FR 8249 then FR 2528 at Madrid
Milan → Madrid → Berlin
Timetable, Madrid time
10:50FR 8249 from Milan at the gate
06:40FR 2528 to Berlin leaves the gate
19 h 50 apart on the timetable, overnight
FR 2528 leaves 19 h 50 after FR 8249 arrives on the timetable: more than half a day, so not a connection we count.