77917-07-8

Basic information

• Product Name: 2,3-Piperazinedione, 1,4-bis(phenylmethyl)-
• CAS NO: 77917-07-8
• Molecular Formula: C18H18N2O2
• Molecular Weight: 294.353
• Mol File: 77917-07-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,3-Piperazinedione, 1,4-bis(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Piperazinedione, 1,4-bis(phenylmethyl)-(77917-07-8)
• EPA Substance Registry System: 2,3-Piperazinedione, 1,4-bis(phenylmethyl)-(77917-07-8)

Safety Data

• Hazardous Substances Data: 77917-07-8(Hazardous Substances Data)

Upstream product

• 1034-11-3 N,N'-dibenzylpiperazine 
• 32705-80-9 1,4-dibenzylpiperazin-2-one 
• 100-46-9 benzylamine 
• 321860-04-2 N-benzyl-N-(2-oxo-ethyl)-oxalamic acid methyl ester 
• 74518-47-1 l'ester methylique de l'acide N benzylhydroxamique 
• 100-39-0 benzyl bromide 
• 63352-56-7 1-benzylpiperazine-2,3-dione 
• 1074-42-6 1-benzylaziridine 

Downstream Products

• 77917-08-9 1,4-bis(4-nitrobenzyl)-2,3-dioxopiperazine 
• 77917-09-0 1,4-bis(4-aminobenzyl)-2,3-dioxopiperazine 
• 77917-10-3 1,4-bis<4-(2-pyrimidinylamino)benzyl>-2,3-dioxopiperazine 
• 63352-56-7 1-benzylpiperazine-2,3-dione 

Relevant articles and documents

Selective, Catalytic, and Dual C(sp3)-H Oxidation of Piperazines and Morpholines under Transition-Metal-Free Conditions

By using cheap and innocuous reagents, such as NaClO2, NaOCl, and catalytic amounts of TEMPO, a new environmentally friendly protocol for the selective and catalytic TEMPO C(sp3)-H oxidation of piperazines and morpholines to 2,3-diketopiperazines (2,3-DKP) and 3-morpholinones (3-MPs), respectively, has been developed. This novel direct access to 2,3-DKP from piperazines provides significant advantages over the traditional N-monoacylation/intramolecular C-N cyclization procedure. Additionally, by modulating the amounts of TEMPO, 2-alkoxyamino-3-morpholinone can be prepared from morpholine derivatives, which would enable further functionalization at the C2 position of the morpholine skeleton.

Piperazines as model substrate for oxidations

Piperazine derivatives when being oxidized by mercury-EDTA behave unusually. Due to the reactive cyclic enediamine intermediates as aza-analogous reductones and to the carbonyl compounds resulting from dehydrogenation in the side chain, there exists a high tendency of polymerization. 1-Benzylpiperazines 5a-d generate the piperazine-2,3-diones 8a-d in medium yields. From 1-benzhydrylpiperazine 11 results a mixture of piperazine-2,3-dione 12 and piperazine-3-on 13. The 1,4-bis-substituted piperazines react more differently because of the symmetry and the preferred direction of the dehydrogenation into the cycle. Thus, from 15 and 19 the diones 16 and 20, respectively, were available in very good yields. A mechanism for the reactions is proposed.

Efficient synthesis of unsymmetrical 1,4-disubstituted-2,3-diketopiperazines via tandem reductive amination-cyclization

Herein we report the efficient syntheses of 1,4-disubstituted-2,3-diketopiperazines and 1,4,5-trisubstituted-2,3-diketopiperazines, which feature a tandem reductive amination and acylation. Aliphatic and aromatic primary amines serve as viable nucleophiles under the mild reaction conditions. (C) 2000 Elsevier Science Ltd.