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AT his age he should be.taking two naps, timing is very important so two hours after he wakes up in the morning you should start putting him for his first nap then a secondd nap almost three hours after he wakes up From his first nap if he is not tired then he will not take a long time to doze off hence it will be easier if he is already tired when u put him down then it will take longer. Also have a quiet environment and dim lights helps.