In 1965,Journal of Medicinal Chemistry included an article by Hermans, Bert; Daele, Paul van; Westeringh, Cornelis van de; Eycken, Cyriel van der; Boey, Jozef; Janssen, Paul A. J.. Application In Synthesis of 4-Amino-1-benzylpiperidine-4-carbonitrile. The article was titled 《4-Substituted piperidines. II. Reaction of 1-benzyl-4-cyano-4-tertiaryaminopiperidines with organometallic compounds》. The information in the text is summarized as follows:
cf. CA 61, 10652f. The reaction of 1-benzyl-4-cyano-4-tertiary-aminopiperidines with organomagnesium and organolithium compounds is described. Reaction of these α-amino nitriles with Grignard reagents results in replacement of the nitrile group, whereas with the organolithium compounds normal ketone formation takes place. The resulting products are debenzylated, whereafter other substituents are introduced. Some of the obtained products show central nervous system depressant activity. In the part of experimental materials, we found many familiar compounds, such as 4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5Application In Synthesis of 4-Amino-1-benzylpiperidine-4-carbonitrile)
4-Amino-1-benzylpiperidine-4-carbonitrile(cas: 136624-42-5) belongs to anime. Nitrous acid converts secondary amines (aliphatic or aromatic) to N-nitroso compounds (nitrosamines): R2NH + HNO2 → R2N―NO. Some nitrosamines are potent cancer-inducing substances, and their possible formation is a serious consideration when nitrites, which are salts of nitrous acid, are present in foods or pharmaceutical preparations. Tertiary amines give rise to nitrosamines more slowly; an alkyl group is eliminated as an aldehyde or ketone, along with nitrous oxide, N2O.Application In Synthesis of 4-Amino-1-benzylpiperidine-4-carbonitrile
Referemce:
Piperidine – Wikipedia,
Piperidine | C5H11N – PubChem