216532-43-3

Basic information

• Product Name: (2R,5S)-1-benzyl-2,5-dimethylpiperazine
• Synonyms: (2R,5S)-1-Benzyl-2,5-dimethylpiperazine;(2R,5S)-2,5-Dimethyl-1-benzyl-piperazine;(2R,5S)-Benzyl 2,5-Dimethylpiperazine-1-
• CAS NO: 216532-43-3
• Molecular Formula: C₁₃H₂₀N₂
• Molecular Weight: 204.315
• Mol File: 216532-43-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 291.506 °C at 760 mmHg
• Flash Point: 109.461 °C
• Appearance: /
• Density: 0.964 g/cm³
• Vapor Pressure: 0.002mmHg at 25°C
• Refractive Index: 1.516
• PKA: 9.35±0.60(Predicted)
• CAS DataBase Reference: (2R,5S)-1-benzyl-2,5-dimethylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,5S)-1-benzyl-2,5-dimethylpiperazine(216532-43-3)
• EPA Substance Registry System: (2R,5S)-1-benzyl-2,5-dimethylpiperazine(216532-43-3)

Safety Data

• Hazardous Substances Data: 216532-43-3(Hazardous Substances Data)

Usage

General Description

(2R,5S)-1-Benzyl-2,5-dimethylpiperazine is a piperazine derivative that contains a benzyl group and two methyl groups attached to the piperazine ring. It is a chiral compound, with a specific orientation of the benzyl and methyl groups. This chemical compound has potential pharmacological activities and is used as a building block in the synthesis of various pharmaceutical compounds. It has been studied for its potential use in medicinal chemistry and drug development due to its unique structural properties and biological activities. The synthesis and study of (2R,5S)-1-Benzyl-2,5-dimethylpiperazine contributes to the development of new drugs and pharmaceuticals.

InChI:InChI=1/C13H20N2/c1-11-9-15(12(2)8-14-11)10-13-6-4-3-5-7-13/h3-7,11-12,14H,8-10H2,1-2H3/t11-,12+/m0/s1

Upstream product

• 100-39-0 benzyl bromide 
• 2815-34-1 2,5-dimethyl-piperazine 
• 1072102-01-2 (3S,6R)-4-benzyl-3,6-dimethylpiperazine-2,5-dione 
• 100-44-7 benzyl chloride 
• 262295-89-6 (3S,6R)-1-benzyl-3,6-dimethylpiperazine-2,5-dione 
• 3138-88-3 (+/-)-trans-2,5-dimethyl-4-benzyl-piperazine 

Downstream Products

• 648423-54-5 4-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-methylbenzonitrile 
• 648423-52-3 4-[(2S,5R)-4-benzyl-2,5-dimethylpiperazin-1-yl]-2-fluorobenzonitrile 
• 253801-16-0 tert-butyl 5-[(R)-[(2S,5R)-4-benzyl-2,5-dimethylpiperazinyl](3-methoxyphenyl)methyl]-1,3-dihydro-2H-isoindole-2-carboxylate 
• 253801-25-1 C₃₅H₄₅N₃O₃ 
• 431062-00-9 4-benzyl-2R,5S-dimethyl-piperazine-1-carboxylic acid tert-butyl ester 
• 243982-58-3 Nov₃r 
• 262295-87-4 (+)-(2S,5R)-4-(2,5-dimethylpiperazin-1-yl)-2-(trifluoromethyl)benzonitrile 
• 262295-90-9 (2S,5R)-4-(4-benzyl-2,5-dimethylpiperazin-1-yl)-2-trifluoromethylbenzonitrile 

Relevant articles and documents

CARBINOL DERIVATIVES HAVING HETEROCYCLIC LINKER

[Object] It is to provide a novel LXRβ agonist useful as a preventative and/or therapeutic agent for atherosclerosis; arteriosclerosis such as those resulting from diabetes; dyslipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases that are caused by inflammatory cytokines; skin diseases such as allergic skin diseases; diabetes; or Alzheimer's disease. [Solving Means] A carbinol compound represented by the following general formula (I) or salt thereof, or their solvate: (wherein, each V and W independently show N or C—R7; each X and Y independently show CH2, C═O, SO2, etc; Z shows CH or N; each R1, R2 and R7 independently show a hydrogen atom, C1-8 alkyl group, etc.; R3 shows C1-8 alkyl group; R4 shows an optionally substituted C6-10 aryl group or an optionally substituted 5- to 11-membered heterocyclic group; R5 and R6 show a hydrogen atom, etc.; L shows a C1-8 alkyl chain optionally substituted with an oxo group, etc.; and n shows any integer of 0 to 2.)

(+)-(2R,5S)-4-[4-cyano-3-(trifluoromethyl)phenyl]-2,5-dimethyl-N-[6- (trifluoromethyl)pyridin-3-yl]piperazine-1-carboxamide (YM580) as an orally potent and peripherally selective nonsteroidal androgen receptor antagonist

A novel series of trans-N-aryl-2,5-dimethylpiperazine-1-carboxamide derivatives was synthesized and their androgen receptor (AR) antagonist activities and in vivo antiandrogenic effects were evaluated. Pharmacological assays indicated that compound 33 was a potent AR antagonist, and subsequent optical resolution provided (+)-(2R,5S)4-[4-cyano-3-(trifluoromethyl)phenyl]-2, 5-dimethyl-N-[6(triflouromethyl)pyridin-3-yl]piperazine-1-carboxamide (33a, YM580) which exhibited the most potent antiandrogenic activity. Unlike bicalutamide, compound 33a decreased the weight of rat ventral prostate in a dose-dependent manner (ED50 = 2.2 mg/kg/day), and induced the maximum antiandrogenic effect, comparable to that of surgical castration, without significantly affecting serum testosterone levels. Compound 33a is a promising clinical candidate for prostate cancer monotherapy.

Cyanophenyl derivative

This application relates to a piperazino-substituted novel cyanophenyl derivative in which a substituted carbamoyl or substituted sulfamoyl group having an aryl, heterocyclic or the like group that may have a substituent group is bonded to one nitrogen atom on the piperazine ring. The compound of this application has an anti-androgen action and is useful in preventing or treating prostatic cancer, benign prostatic hyperplasia and the like diseases.