81577-03-9

Upstream product

• 5400-82-8 N,N-dimethylbenzylamine N-oxide 
• 100-52-7 benzaldehyde 
• 110-70-3 N,N`-dimethylethylenediamine 
• 70708-34-8 (±)-2,3-diphenylpiperazine 
• 74-88-4 methyl iodide 
• 104-71-2 N,N'-bis(benzyliden)ethylendiamine 
• 81577-01-7 piperazine-2,3 diphenyl N,N-dimethyl cis 

Relevant academic research and scientific papers

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.

Deprotonation de N-oxydes d'amines aliphatiques: schema reactionnel general et nouvelle synthese de pyrrolidines

Amine oxides, 1, 5, 10, 15, 21, 23, when treated by lithium diisopropylamide undergo deprotonation.Monodeprotonation gives rise either to secondary amines and benzaldehyde resulting from the hydrolysis of an intermediate immonium (I) or to hydroxylamines via a Stevens-like rearrangement observed for the first time on an amine oxide.Double deprotonation gives an immonium ylid (Y) which, depending upon the structure of the initial tertiary amine yields either "head to head" piperazines (biradical-like behavior of (DD)) or aziridines.The immonium ylid (Y5) derived from trimethylamine oxide, whose formation and reactivity are reported for the first time, has remarkable property of undergoing cycloaddition reactions with unactivated olefins, leading to a new and efficient synthesis of various pyrrolidines.

Electrochemical Reduction of Di-Schiff Bases. Synthesis of Piperazines, Indoloindoles, Diazepines, and Diazocines

The electrochemical reduction of a series of di-Schiff bases had led to examples where products representing reduction, cyclization, and transannular cyclization are found.Useful synthetic pathways for piperazines, indoloindoles, diazepines, and diazocines are described.

PHOTOCHEMICAL CIS, TRANS-ISOMERIZATION IN THE 2,3-DIPHENYLPIPERAZINE SERIES

Irradiation of cis diphenyl substituted piperazines 2a, b (R = Me, H) in acetonitrile solution results in their conversion to trans compounds 1a, b (R = Me, H) while in the case of 2c (R = CH2Ph) no isomerization is observed.On the other hand, none of the three trans-piperazines isomerizes under the same conditions.A general mechanism is proposed.

The Reactivity of Benzyldimethylamine N-Oxide on Treatment with Strong Bases

Treatment of the title compound with lithium amide or n-butyl-lithium has revealed a hitherto unknown radical type reactivity for benzylic amine oxides.