Syntheses of N-alkyl-N-(hydroxy- or oxo-alkyl)nitrosamines related to N-butyl-N-(4-hydroxybutyl)nitroamine, a potent bladder carcinogen.

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Abstract
N-alkyl-N-(hydroxy- or oxo-alkyl)nitrosamines (19) structurally related to N-butyl-N-(4-hydroxybutyl)nitrosamine, a potent bladder carcinogen, were synthesized for the purpose of investigating their carcinogenic effects in rats. They are N-alkyl-N-(4-hydroxybutyl)nitrosamines, N-alkyl-(3-hydroxypropyl)-nitrosamines, N-alkyl-N-(2-hydroxyalkyl)nitrosamines and N-alkyl-N-(2- or 3-oxoalkyl)nitrosamines. Most were prepared by the nitrosation of the corresponding N-alkyl-N-(hydroxyalkyl)amines. The nitrosamines with an oxo group were prepared by CrO3 oxidation of the corresponding N-alkyl-N-(hydroxyalkyl)nitrosamines with a secondary hydroxyl group.