New approach for induction of alkyl moiety to aliphatic amines by NaBH(OAc)3 with carboxylic acid

We had found the novel N-alkylation method, which utilizes carboxylic acids as alkyl sources with sodium triacetoxyborohydride [NaBH(OAc)3]. Our methodology had been revealed to have some advantages over the reported similar procedures. Through the further investigation about our method, it was disclosed that acetonitrile was the suitable solvent and N-alkylation for aliphatic amines were also smoothly proceeded. On the way of the research, we discovered that 4-hydroxybutyl moiety was induced to aniline by use of old THF containing peroxidic materials.