Further investigation of the synthesis of (8) showed that after 2h little of the product had been formed, yet no (3) remained. Work-up provided the chloropyridine (13) in 80% yield and further heating of (13) with morpholine (18h, 190°, NMP) gave (8) as before. Thus it would appear that under basic conditions, N-deoxygenation occurs first followed by nucleophilic displacement on the less activated pyridine. ... For the more volatile amines it was desirable to develop a ...
