170701-81-2

Basic information

• Product Name: 1,4-Bis(phenylmethyl)-2-piperazinecarbonitrile
• Synonyms: 1,4-Bis(phenylmethyl)-2-piperazinecarbonitrile;1,4-Dibenzylpiperazine-2-carbonitrile
• CAS NO: 170701-81-2
• Molecular Formula: C₁₉H₂₁N₃
• Molecular Weight: 291.39014
• Mol File: 170701-81-2.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 447.223 °C at 760 mmHg
• Flash Point: 191.583 °C
• Appearance: /
• Density: 1.15 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.625
• CAS DataBase Reference: 1,4-Bis(phenylmethyl)-2-piperazinecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Bis(phenylmethyl)-2-piperazinecarbonitrile(170701-81-2)
• EPA Substance Registry System: 1,4-Bis(phenylmethyl)-2-piperazinecarbonitrile(170701-81-2)

Safety Data

• Hazardous Substances Data: 170701-81-2(Hazardous Substances Data)

Usage

General Description

"1,4-Bis(phenylmethyl)-2-piperazinecarbonitrile" is a chemical compound with the molecular formula C20H20N4. It is a piperazine derivative that contains two phenylmethyl groups and a cyano group. This chemical is commonly used as a building block in organic synthesis to create various pharmaceuticals, agrochemicals, and other functional materials. It has also been studied for its potential pharmacological activities, including as an antipsychotic and anxiolytic agent. However, its specific uses and biological effects may vary depending on its chemical structure and formulation. Nevertheless, "1,4-Bis(phenylmethyl)-2-piperazinecarbonitrile" is a valuable and versatile chemical that is used in various scientific and industrial applications.

InChI:InChI=1/C19H21N3/c20-13-19-16-21(14-17-7-3-1-4-8-17)11-12-22(19)15-18-9-5-2-6-10-18/h1-10,19H,11-12,14-16H2

Upstream product

• 4554-16-9 2,3-dibromopropionitrile 
• 140-28-3 N,N'-Dibenzylethylenediamine 
• 122-75-8 N,N'-dibenzylethylenediamine diacetate 
• 14165-27-6 N,N-dibenzylethylenediamine 
• 920-37-6 2-Chloroacrylonitrile 

Downstream Products

• 116163-33-8 2-aminomethyl-1,4-di-phenylmethyl piperazine 
• 253873-06-2 1,4-dibenzyl-2-(isopropyloxycarbonylaminomethyl)piperazine 
• 253873-10-8 1,4-dibenzyl-2-(2,2-dimethylpropionylaminomethyl)piperazine 
• 124257-72-3 2-<(acetylamino)methyl>-1,4-dibenzylpiperazine 

Relevant articles and documents

Some N-mono- and N, N'-disubstituted derivatives of 2- piperazinecarbonitrile

Five new 4-R1-mono- and 1-R1-4-R2- disubstituted derivatives (R1, R2 = benzyl, benzoyl) of 2-piperazinecarbonitrile were synthesized and fully characterized by PMR and CMR spectral methods. By comparison with model compounds, a preferred axial position was advanced for the cyano group. Substitution of the aminic hydrogen atom by a benzyl or benzoyl group affected the NMR chemical shifts of all piperazine atoms. Careful spectral analysis gave the respective Δδh and Δδc increments, useful in stereochemical assignments. The protons in α with respect to the introduced N- benzyl group were shielded by about 0.4 ppm and the corresponding carbons deshielded by about 6 ppm. The most affected were the axial N-α-protons (Δδh ～ 0.55 ppm). If the N-substituent was benzoyl, the piperazine N-α-protons were largely deshielded, especially those pseudo-equatorially located (by 1.0-1.1 ppm). The NMR shifts were interpreted in terms of through-bond (i.e., inductive) and through-space effects exerted by the introduced N-substituent.

Piperazine derivatives inhibiting human immunodeficiency virus replication

The invention concerns the use of a piperazine derivative of formula (I) wherein: A and B=C═O, C═S or CR7R8with R7=H, methyl, cyano, cyanomethyl, CO2CH3or (C═O)CH3and R8=H or phenyl; R1to R6=H, OH, or C1-C5alkoxy; X represents: either C═O, O(C═O), O(C═S), O(SO2), NH(C═O), NH(C═S), NH(SO2), S(C═O) or S(C═S), then Y=NR9R10, CR9R10R11in which R9, R10and R11=H, C1-C5alkyl, C2-C5alkenyl, or C2-C5alkynyl or Y=nitrogenous heterocycle comprising 5 to 10 atoms; or X represents O, S, O(C═O)O, NH(C═O)O, or S(C═O)O, then Y=CR9R10R11with R9, R10, R11as above; or one of its pharmaceutically acceptable salts for preparing a medicine inhibiting HIV. The invention is useful for treating HIV infection.

Design and synthesis of imidazoline derivatives active on glucose homeostasis in a rat model of type ii diabetes. 2. Syntheses and biological activities of 1,4-dialkyl-, 1,4-dibenzyl, and 1-benzyl-4-alkyl-2-(4',5'- dihydro-1'H-imidazol-2'-yl)piperazines and isosteric analogues of imidazoline

Piperazine derivatives have been identified as new antidiabetic compounds. Structure-activity relationship studies in a series of 1-benzyl- 4-alkyl-2-(4',5'-dihydro-1'H-imidazol-2'-yl)piperazines resulted in the identification of 1-methyl-4-(2',4'-dichlorobenzyl)-2-(4',5'-dihydro-1'H- imidazol-2'-yl)piperazine, PMS 812 (S-21663), as a highly potent antidiabetic agent on a rat model of diabetes, mediated by an important increase of insulin secretion independently of α2 adrenoceptor blockage. These studies were extended to find additional compounds in these series with improved properties. In such a way, substitution of both piperazine N atoms was first optimized by using various alkyl, branched or not, and benzyl groups. Second, some modifications of the imidazoline ring and its replacement by isosteric heterocycles were carried out, proceeding from PMS 812, to evaluate their influence on the antidiabetic activity. The importance of the distance between the imidazoline ring and the piperazine skeleton was studied third. Finally, the influence of the N-benzyl moiety was also analyzed compared to a direct N-phenyl substitution. The pharmacological evaluation was performed in vivo using glucose tolerance tests on a rat model of type II diabetes. The most active compounds were 1,4-diisopropyl-2-(4',5'-dihydro-1'H-imidazol-2'- yl)piperazine (41a), PMS 847 (S-22068), and 1,4-diisobutyl-2-(4',5'-dihydro- 1'H-imidazol-2'-yl)piperazine (41b), PMS 889 (S-22575), which strongly improved glucose tolerance without any side event or hypoglycemic effect. More particularly, PMS 847 proved to be as potent after po (100 μmol/kg) as after ip administration and appears as a good candidate for clinical investigations.