137407-00-2Relevant academic research and scientific papers
Convenient preparations of imines and symmetrical secondary amines possessing primary or secondary alkyl groups
Katritzky,Zhao,Hitchings
, p. 703 - 708 (2007/10/02)
Hindered alkyl aldehydes react with benzotriazole and ammonia in dry ethanol or methanol to yield the corresponding bis[1-(benzotriazol-1-yl)alkyl]amines 2. The reaction of aryl aldehydes, however, yields 1-(benzotriazol-1-yl)-N-alkylidenealkylamines 3. The reactions of adducts 2 and 3 with lithium aluminum hydride furnishes dialkyl- and dibenzylamine derivatives 4. Although the reactions of 2 and 3 with organometallic reagents are not as general, in several cases the reactions of amines 2 with Grignard reagents yield 1-alkyl or aryl substituted N-alkylidenealkylamines 5. Similar reactions of amines 2 with phenyl lithium afford 1,1'-diphenyldialkylamines 7.
