23173-57-1

Basic information

• Product Name: 1-(4-METHYLBENZYL)PIPERAZINE
• Synonyms: TIMTEC-BB SBB003648;1-(4-METHYLBENZYL)PIPERAZINE;AKOS B004004;AKOS BBS-00003645;BUTTPARK 36\08-62;ART-CHEM-BB B004004;Methylbenzylpiperazine;1-(4-Methylbenzyl)piperazine 98%
• CAS NO: 23173-57-1
• Molecular Formula: C₁₂H₁₈N₂
• Molecular Weight: 190.28
• Product Categories: Building Blocks;Heterocyclic Building Blocks;Piperazines
• Mol File: 23173-57-1.mol
• Article Data: 19

Chemical Properties

• Melting Point: 37-41 °C(lit.)
• Boiling Point: 115-117°C 1mm
• Flash Point: 205 °F
• Appearance: /
• Density: 1.011 g/cm³
• Vapor Pressure: 0.00192mmHg at 25°C
• Refractive Index: 1.543
• PKA: 9.16±0.10(Predicted)
• CAS DataBase Reference: 1-(4-METHYLBENZYL)PIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-METHYLBENZYL)PIPERAZINE(23173-57-1)
• EPA Substance Registry System: 1-(4-METHYLBENZYL)PIPERAZINE(23173-57-1)

Safety Data

• Hazard Codes: Xi
• Statements: 37/38-41
• Safety Statements: 26-39
• WGK Germany: 2
• HazardClass: IRRITANT
• Hazardous Substances Data: 23173-57-1(Hazardous Substances Data)

Usage

Description

1-(4-Methylbenzyl)piperazine is an organic compound that serves as a valuable synthetic intermediate in the pharmaceutical industry. It is characterized by its chemical structure, which includes a piperazine ring with a 4-methylbenzyl group attached to it. This unique structure endows it with specific properties that make it useful in the development of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Synthesis:
1-(4-Methylbenzyl)piperazine is used as a synthetic intermediate for the development of 3-Desmethyl 4-Methyl Meclizine Dihydrochloride, which is a metabolite of Meclizine (2HCl monohydrate). Meclizine is an antiemetic medication used to treat nausea, vomiting, and dizziness caused by motion sickness, vertigo, or Meniere's disease.
Used in Antiemetic Applications:
1-(4-Methylbenzyl)piperazine is used as a precursor in the pharmaceutical industry for the synthesis of antiemetic agents. Its role in the production of Meclizine, an effective antiemetic, highlights its importance in addressing the symptoms of motion sickness, vertigo, and Meniere's disease.
Used in Enzyme Inhibitor Synthesis:
1-(4-Methylbenzyl)piperazine is also used as a synthetic intermediate in the development of inhibitors for acetylcholinesterase (AChE) and butyrylcholinesterase. These enzymes are involved in the breakdown of acetylcholine, a neurotransmitter that plays a crucial role in various cognitive functions and muscle contractions. Inhibiting these enzymes can help improve cognitive function and memory in conditions like Alzheimer's disease and other neurodegenerative disorders.

InChI:InChI=1/C12H18N2/c1-11-2-4-12(5-3-11)10-14-8-6-13-7-9-14/h2-5,13H,6-10H2,1H3

Upstream product

• 104-82-5 4-Methylbenzyl chloride 
• 110-85-0 piperazine 
• 104-87-0 4-methyl-benzaldehyde 
• 104-81-4 4-Methylbenzyl bromide 
• 111752-26-2 piperazin-1-yl(p-tolyl)methanone 
• 779989-61-6 1,1-dimethylethyl 4-[(4-methylphenyl)methyl]-1-piperazine carboxylate 

Downstream Products

• 79837-40-4 1-(3-hydroxypropyl)-4-(4-methylbenzyl)piperazine 
• 112291-99-3 1-benzhydryl-4-(4-methyl-benzyl)-piperazine 
• 307335-57-5 3-[4-(4-methyl-benzyl)-piperazin-1-yl]-1,3-dihydro-indol-2-one 
• 307335-65-5 3-[4-(4-methyl-benzyl)-piperazin-1-yl]-1,3,4,5-tetrahydro-benzo[b]azepin-2-one 
• 313235-07-3 1-((2S)-2-vinylindolinyl)-2-{4-[(4-methylphenyl)methyl]piperazinyl}ethan-1-one 
• 946522-98-1 benzyl ester of {2-[4-(4-methylbenzyl)piperazin-1-yl]-2-oxoethyl}carbamic acid 
• 79837-43-7 5-Methyl-6-{3-[4-(4-methyl-benzyl)-piperazin-1-yl]-propoxy}-1H-4-oxa-1,2,3-triaza-cyclopenta[b]naphthalen-9-one 
• 79837-41-5 1-(4-Methoxy-benzyl)-5-methyl-6-{3-[4-(4-methyl-benzyl)-piperazin-1-yl]-propoxy}-1H-4-oxa-1,2,3-triaza-cyclopenta[b]naphthalen-9-one 
• 79837-42-6 2-(4-Methoxy-benzyl)-5-methyl-6-{3-[4-(4-methyl-benzyl)-piperazin-1-yl]-propoxy}-2H-4-oxa-1,2,3-triaza-cyclopenta[b]naphthalen-9-one 
• 779989-61-6 1,1-dimethylethyl 4-[(4-methylphenyl)methyl]-1-piperazine carboxylate 

Relevant articles and documents

Zirconium-hydride-catalyzed site-selective hydroboration of amides for the synthesis of amines: Mechanism, scope, and application

Developing mild and efficient catalytic methods for the selective synthesis of amines is a longstanding research objective. In this respect, catalytic deoxygenative amide reduction has proven to be promising but challenging, as this approach necessitates selective C–O bond cleavage. Herein, we report the selective hydroboration of primary, secondary, and tertiary amides at room temperature catalyzed by an earth-abundant-metal catalyst, Zr-H, for accessing diverse amines. Various readily reducible functional groups, such as esters, alkynes, and alkenes, were well tolerated. Furthermore, the methodology was extended to the synthesis of bio- and drug-derived amines. Detailed mechanistic studies revealed a reaction pathway entailing aldehyde and amido complex formation via an unusual C–N bond cleavage-reformation process, followed by C–O bond cleavage.

Discovery of Novel Apigenin-Piperazine Hybrids as Potent and Selective Poly (ADP-Ribose) Polymerase-1 (PARP-1) Inhibitors for the Treatment of Cancer

Poly (ADP-ribose) polymerase-1 (PARP-1) is a potential target for the discovery of chemosensitizers and anticancer drugs. Amentoflavone (AMF) is reported to be a selective PARP-1 inhibitor. Here, structural modifications and trimming of AMF have led to a series of AMF derivatives (9a-h) and apigenin-piperazine/piperidine hybrids (14a-p, 15a-p, 17a-h, and 19a-f), respectively. Among these compounds, 15l exhibited a potent PARP-1 inhibitory effect (IC50 = 14.7 nM) and possessed high selectivity to PARP-1 over PARP-2 (61.2-fold). Molecular dynamics simulation and the cellular thermal shift assay revealed that 15l directly bound to the PARP-1 structure. In in vitro and in vivo studies, 15l showed a potent chemotherapy sensitizing effect against A549 cells and a selective cytotoxic effect toward SK-OV-3 cells through PARP-1 inhibition. 15l·2HCl also displayed good ADME characteristics, pharmacokinetic parameters, and a desirable safety margin. These findings demonstrated that 15l·2HCl may serve as a lead compound for chemosensitizers and the (BRCA-1)-deficient cancer therapy.

Genipin analogue, preparation method and application thereof

The invention relates to the field of pharmaceutical chemistry, and in particular relates to genipin analogues (I) and medicinal salts containing the genipin analogues, a preparation method and pharmaceutical compositions containing the genipin analogues or the medicinal salts. Pharmacodynamic tests prove that the compounds provided by the invention can be used for preventing and treating neurodegenerative diseases such as Alzheimer.