I would say no more than an hr. That's what I did with my 4 kids,and it worked....
If your little one has teeth, he or she should only get water to drink at night (my nephew had to have crowns put in because of tooth decay from nighttime food!) and if water is what you are giving him at night a bottle won't hurt anything. A sippy cup is awfully messy at night, it's really for drinking sitting up. The baby might be crying because it's leaking.
We transitioned my son off a night bottle (of formula) to a night bottle of water, and then he transitioned himself off the water because it wasn't as yummy as the milk. No crying.
If your child is crying because he is hungry, that is another issue.
Be sure to brush his teeth as soon as they arrive.
Feed him some solid food before bedtime to make sure he's full and lay with him until he falls asleep..it worked with my daughter