FR 270 then IB 414 at Barcelona
Milan → Barcelona → Madrid
Timetable, Barcelona time
17:45FR 270 from Milan at the gate
15:05IB 414 to Madrid leaves the gatealso LA 1557, LL 3014, VY 5062, QR 6557, BA 7082, CZ 7324
21 h 20 apart on the timetable, overnight
IB 414 leaves 21 h 20 after FR 270 arrives on the timetable: more than half a day, so not a connection we count.