77069-67-1

Upstream product

• 107-31-3 Methyl formate 
• 694-83-7 rac-diaminocyclohexane 
• 1436-59-5 cis-cyclohexane-1,2-diamine 
• 109-94-4 formic acid ethyl ester 

Downstream Products

• 75599-23-4 (1R,2S)-N¹,N²- dimethylcyclohexane-1,2-diamine 

Relevant academic research and scientific papers

PRODUCTION METHOD OF TRANS-1,2 DIAMINOCYCLOHEXANE

PROBLEM TO BE SOLVED: To provide an industrial production method capable of efficiently producing trans-1,2-diaminocyclohexane from an isomer mixture of trans-1,2-diaminocyclohexane and cis-1,2-diaminocyclohexane. SOLUTION: In a production method of trans-1,2-diaminocyclohexane, an isomer mixture of 1,2-diaminocyclohexanes containing cis-1,2-diaminocyclohexane and trans-1,2-diaminocyclohexane reacts with a blocking agent reactive with an amino group to block two amino groups by a blocking group and is subjected to crystallization in the presence of a base to raise a trans/cis ratio in the isomer mixture of 1,2-diaminocyclohexanes. COPYRIGHT: (C)2016,JPOandINPIT

The copper-catalyzed N-arylation of indoles

A general method for the N-arylation of indoles using catalysts derived from Cul and trans-1,2-cyclohexanediamine (1a), trans-N,N′-dimethyl-1,2-cyclohexanediamine (2a), or N,N′-dimethyl-ethylenediamine (3) is reported. N-Arylindoles can be produced in high yield from the coupling of an aryl iodide or aryl bromide with a variety of indoles.

211. Scope and Limitations of the Reductive Coupling of Aromatic Aldimine Derivatives with Formation of 1,2-Diarylethylenediamine Units, Using Low-Valent Titanium Reagents

Besides the adducts from lithium amides to aromatic aldehydes, iminium salts, aminals, and N-silylimines of aromatic aldehydes are coupled by the black suspension obtained from TiCl4 and Mg turnings in tetrahydrofuran (THF).The 1,2-diarylethylenediamines with tertiary and primary amino groups thus obtained are formed with no or only moderate diastereoselectivity (products 4a-d (Scheme 2) and 5a-e (Scheme 3), respectively); the amine component may contain a strained ring or additional heteroatoms as in azetidin, bis(2-metoxyethyl)amine piperazine, morpholine, and thiomorpholine (products 6a-e; Table 1).By an in-situ procedure, ethylenediamines and propane-1,3-diamines with two secondary amino groups are cyclized with aromatic aldehydes to give exclusively trans-diaryl-substituted piperazine and perhydro-1,4-diazepine derivatives (products 7a-f; Table 2).Enantiomerically pure monocyclic trans,cis-5-alkyl-2,3-diaryl-piperazines and diazabicyclononanes and -decanes are obtained by employing suitable diamines prepared from the amino acids (S)-alanine, (S)-phenylalanine, (S)-proline, and from (S,S)- or (R,R)-cyclohexane-1,2-diamine, respectively (products 11a-i, 7e; Table 4).The configurations of all products are derived from the high-field NMR spectra, some of which are discussed in detail (Figs. 1 and 2, Tables 3 and 5); all new compounds are fully characterized by their physical data.Depending upon the structure of the components employed, the yields of purified products range from as low as 7percent to essentially quantitative.