Effective Synthesis of Deuterated n-Octylamine and Its Analogues

Abstract

In neutron scattering studies, deuterium-labelled compounds play a key role in controlling the contrast of organic samples and reducing the incoherent scattering background from the samples. As amine compounds play a vital role as functional molecules, we have developed a new synthesis method using an amide compound as a starting material to synthesize deuterated amines and their analogues. We determined the deuteration ratio of the obtained deuterated 1-octylamine by mass spectrometry, nuclear magnetic resonance (NMR), and neutron reflectometry techniques. As a result, the deuteration ratio was estimated to be ~60 %. The deuteration ratio of the synthesized 1-octylamine was not high because the method used did not deuterate its α-protons and NH2 group. However, this synthesis method is suitable for the large-scale synthesis of deuterated amine compounds for neutron research because it is easy to increase the synthetic scale.