Starting at 2:15
1 Hour would be 3:15pm
5 Hour would be 7:15pm
8 Hour would be 10:15pm
10 Hour would be 12:15pm
Since 10 Hours gets us too far over our final time we'll use 9 hours
9 Hours gets us to 11:15pm
adding 30 minutes gets us to 11:45 pm
and adding 5 more minutes gets us to our final time of 11:50pm
All in all it takes 9 Hours 35 Minutes from 2:15 pm to 11:50 pm