Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine

Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine used with CuI to form a general and highly efficient catalyst for the N-amidation of aryl and heteroaryl iodides, bromides and in some cases, unactivated aryl chlorides. The catalyst system is also used for the N-arylation of indoles.

Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine is a useful research chemical for organic synthesis and other chemical processes.

trans-N,N′-dimethylcyclohexane-1,2-diamine can be used as a ligand in the synthesis of the following products via copper catalyzed C-N coupling reactions:

• vinylsulfoximines obtained from NH sulfoximes and vinyl bromides
• N-arylpyridones obtained via reaction between 2-substituted pyridines and aryl halides
• N-aryl amines obtained via reaction between amines and aryl iodides/aryl bromides

Cyclohexene oxide (1) was reacted with 25–30% aqueous methylamine (1.5 equiv.) in a sealed reactor to form trans-2-(methylamino)cyclohexanol 2 at 80 °C within 5h. Compound 2 was subjected to Mitsunobu reaction at room temperature, followed by adjusting the pH from 2 to 10 to yield 7-methyl-7-azabicyclo[4.1.0]-heptane 3, which was directly subjected to the following reaction without purification. Ring-opening reactions of compound 3 with a methylamine aqueous solution were completed in a sealed reactor at 110 °C after 6h to yield Trans-(1R,2R)N,N'-Dimethyl-cyclohexane-1,2-diamine.

[1] Patent: CN106478431, 2017, A. Location in patent: Paragraph 0011; 0012; 0013; 0014; 0015; 0016; 0017; 0018