1500084-06-9

Basic information

• Product Name: (R,R)-trans-N,N’-dimethyl-N,N’-bis(pyridin-4-yl)cyclohexane-1,2-diamine
• Synonyms: (R,R)-trans-N,N’-dimethyl-N,N’-bis(pyridin-4-yl)cyclohexane-1,2-diamine
• CAS NO: 1500084-06-9
• Molecular Weight: 296.415
• Mol File: 1500084-06-9.mol

Chemical Properties

• CAS DataBase Reference: (R,R)-trans-N,N’-dimethyl-N,N’-bis(pyridin-4-yl)cyclohexane-1,2-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-trans-N,N’-dimethyl-N,N’-bis(pyridin-4-yl)cyclohexane-1,2-diamine(1500084-06-9)
• EPA Substance Registry System: (R,R)-trans-N,N’-dimethyl-N,N’-bis(pyridin-4-yl)cyclohexane-1,2-diamine(1500084-06-9)

Safety Data

• Hazardous Substances Data: 1500084-06-9(Hazardous Substances Data)

Upstream product

• 1500084-25-2 (R,R)-trans-N,N’’-dimethyl-N,N’’-bis(2,6-difluoropyridin-4-yl)cyclohexane-1,2-diamine 

Relevant articles and documents

Selective catalytic hydrodefluorination as a key step for the synthesis of hitherto inaccessible aminopyridine derivatives

Fluorine makes it possible! The regioselective nucleophilic substitution of (oligo)fluoropyridines with the appropriate amines and the subsequent catalytic hydrodefluorination paves the way to hitherto inaccessible aminopyridine derivatives, which are of interest as new ligands. Up to four fluorine atoms can be removed regioselectively in one step in a reaction employing an inexpensive titanium precatalyst. Copyright

Studies on the Synthesis of Specifically Fluorinated 4-Amino-pyridine Derivatives by Regioselective Nucleophilic Aromatic Substitution and Catalytic Hydrodefluorination

The reactions of pentafluoropyridine and 2,4,6-trifluoropyridine with a series of primary and secondary amines were studied. Whereas the nucleophilic aromatic substitution of pentafluoropyridine occurs with high regioselectivity in all cases, providing the expected 4-aminopyridine derivatives in excellent yields, the regioselectivity of 2,4,6-trifluoropyridine is dependent on the steric hindrance of the attacking nucleophile. Small nucleophiles such as morpholine attack the 4-position of the pyridine ring with high preference, but more bulky diamines attack the 2- and 4-positions leading to the formation of three regioisomeric products. (R,R)-1,2-Diaminocyclohexane as moderately bulky diamine reacted with 2,4,6-trifluoropyridine to afford the desired bis(4-aminopyridinyl)cyclohexane derivative in 30% yield. For hydrodefluorination two methods were examined. A two-step procedure employing hydrazine and subsequently copper(II) sulfate removed just one fluorine substituent, but is not sufficiently high yielding for the reduction of more complex substrates. With the system titanocene difluoride as pre-catalyst and diphenylsilane as reducing agent we were able to selectively remove fluorine substituents at positions C-2 and C-4 of a variety of 4-aminopyridine derivatives. This protocol allows the synthesis of compounds such as the divalent chiral 4-(dimethylamino)pyridine (DMAP) analogue (R,R)-trans-N,N'-dimethyl-N,N'-bis(pyridin-4-yl)cyclohexane-1,2-diamine with fair overall yield.