132871-12-6

Basic information

• Product Name: (S)-2-METHYL-4-BENZYLPIPERAZINE
• Synonyms: (S)-2-METHYL-4-BENZYLPIPERAZINE;4-N-BENZYL-2-(S)-METHYLPIPERAZINE;Piperazine, 3-methyl-1-(phenylmethyl)-, (3S)- (9CI);(3S)-1-BENZYL-3-METHYLPIPERAZINE;1-Benzyl-3(S)-methylpiperazine;(3S)-3-Methyl-1-(phenylmethyl)piperazine;AB3085;(3S)-3-Methyl-1-(phenylmethyl)piperazine,99%e.e.
• CAS NO: 132871-12-6
• Molecular Formula: C₁₂H₁₈N₂
• Molecular Weight: 190.28
• Product Categories: PIPERIDINE;pharmacetical
• Mol File: 132871-12-6.mol

Chemical Properties

• Melting Point: 31-33 °C
• Boiling Point: 282℃
• Flash Point: 112℃
• Appearance: /
• Density: 0.991
• Vapor Pressure: 0.00354mmHg at 25°C
• Refractive Index: 1.529
• PKA: 9.31±0.40(Predicted)
• CAS DataBase Reference: (S)-2-METHYL-4-BENZYLPIPERAZINE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-METHYL-4-BENZYLPIPERAZINE(132871-12-6)
• EPA Substance Registry System: (S)-2-METHYL-4-BENZYLPIPERAZINE(132871-12-6)

Safety Data

• Hazardous Substances Data: 132871-12-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
(S)-2-METHYL-4-BENZYLPIPERAZINE is used as a key intermediate in the synthesis of various pharmaceutical drugs and biologically active molecules. Its unique structure allows for the creation of compounds with potential therapeutic properties.
Used in Therapeutic Applications:
In the medical field, (S)-2-METHYL-4-BENZYLPIPERAZINE is used as a potential treatment for conditions such as anxiety, depression, and neurological disorders. Its pharmacological properties are being studied for their ability to address these health issues effectively.
Used as a Drug Delivery Vehicle:
(S)-2-METHYL-4-BENZYLPIPERAZINE has been investigated for its potential as a drug delivery vehicle. Its structure may facilitate the targeted delivery of therapeutic agents, improving the efficacy and reducing the side effects of treatments.
Used as a Targeting Ligand in Drug Design:
Furthermore, (S)-2-METHYL-4-BENZYLPIPERAZINE is utilized as a targeting ligand in drug design. This application takes advantage of its ability to bind specifically to certain biological targets, thereby enhancing the selectivity of drug action and potentially leading to more effective therapies.
Overall, (S)-2-METHYL-4-BENZYLPIPERAZINE is a versatile compound that plays a crucial role in the development of new pharmaceutical compounds and drug delivery systems, offering promising avenues for improving patient care and treatment outcomes.

InChI:InChI=1/C12H18N2/c1-11-9-14(8-7-13-11)10-12-5-3-2-4-6-12/h2-6,11,13H,7-10H2,1H3/t11-/m0/s1

Upstream product

• 118375-95-4 methyl (S)-2-(2-chloroacetamido)propanoate 
• 104-63-2 N-Benzylethanolamine 
• 100-46-9 benzylamine 
• 86666-85-5 N^α-Boc-Ala-N^α-benzylglycine ethyl ester 
• 761357-45-3 [((S)-2-Amino-propionyl)-benzyl-amino]-acetic acid ethyl ester 
• 6436-90-4 ethyl 2-(benzylamino)acetate 
• 132871-10-4 (3S)-1-benzyl-3-methylpiperazine-2,5-dione 
• 170033-57-5 (S)-3-Methyl-1-(phenylmethyl)piperazin-2-one 
• 74879-18-8 (S)-2-methylpiperazine 
• 100-39-0 benzyl bromide 
• 170033-54-2 (S)-<2-<(2-Hydroxyethyl)(phenylmethyl)amino>-1-methyl-2-oxoethyl>carbamic acid 1,1-dimethylethyl ester 

Downstream Products

• 400786-02-9 (S)-2-(4-benzyl-2-methyl-piperazin-1-yl)-quinoxaline 
• 400786-01-8 (S)-2-(4-benzyl-2-methyl-piperazin-1-yl)-oxazolo[5,4-c]pyridine 
• 400785-78-6 1R-[4-(4-benzyl-2S-methyl-piperazin-1-yl)pyrimidin-2-yl]ethyl butyrate 
• 1018829-31-6 (2S)-4-benzyl-1-(4-bromo-3-methylphenyl)-2-methylpiperazine 
• 300552-28-7 (S)-2-(4-benzyl-2-methyl-piperazin-1-yl)-oxazolo[5,4-b]pyridine 
• 511255-00-8 4-(4-chloro-phenyl)-3-(S)-methyl-piperazine 
• 169447-70-5 (S)-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 511254-97-0 (S)-4-benzyl-1-(4-chlorophenyl)-2-methylpiperazine 
• 400785-91-3 (S)-2-(4-benzyl-2-methyl-piperazin-1-yl)-4-methoxymethyl-6-methyl-pyrimidine 
• 169447-69-2 tert-Butyl (S)-2-methyl-4-(phenylmethyl)-1-piperazinecarboxylate 

Relevant articles and documents

Structure-Activity Relationship Studies on Oxazolo[3,4- a]pyrazine Derivatives Leading to the Discovery of a Novel Neuropeptide S Receptor Antagonist with Potent in Vivo Activity

Neuropeptide S modulates important neurobiological functions including locomotion, anxiety, and drug abuse through interaction with its G protein-coupled receptor known as neuropeptide S receptor (NPSR). NPSR antagonists are potentially useful for the treatment of substance abuse disorders against which there is an urgent need for new effective therapeutic approaches. Potent NPSR antagonists in vitro have been discovered which, however, require further optimization of their in vivo pharmacological profile. This work describes a new series of NPSR antagonists of the oxazolo[3,4-a]pyrazine class. The guanidine derivative 16 exhibited nanomolar activity in vitro and 5-fold improved potency in vivo compared to SHA-68, a reference pharmacological tool in this field. Compound 16 can be considered a new tool for research studies on the translational potential of the NPSergic system. An in-depth molecular modeling investigation was also performed to gain new insights into the observed structure-activity relationships and provide an updated model of ligand/NPSR interactions.

Efficient one-pot synthesis of enantiomerically pure: N -protected-α-substituted piperazines from readily available α-amino acids

A new pathway towards enantiomerically pure 3-substituted piperazines, bearing a benzyl protecting group, has been developed in good overall yields (83-92%), starting from commercially available N-protected amino acids. The methodology represents an efficient and simple one-pot procedure, employing a synthetic sequence consisting of an Ugi-4 component reaction, a Boc-deprotection, an intramolecular cyclisation reaction and a final reduction (UDCR). From the benzyl protected precursors, the 2-substituted piperazines bearing a Boc-protecting group could consequently also be obtained via a simple protection and deprotection step of the corresponding piperazines. The practical utility of this methodology was demonstrated for chiral drug synthesis.

Enantiomerically pure piperazines via NaBH4/I2reduction of cyclic amides

Enantiomerically pure (3S,7R,8aS)-3-phenyloctahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-methyl octahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-isopropyloctahydropyrrolo[1,2-a]pyrazine-7-ol and (3S,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol 16d were synthesized via preparation of the corresponding cyclic amides from enantiomerically pure L-proline and hydroxyproline derivatives followed by reduction using sodium borohydride-iodine.

Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics

(Chemical Equation Presented) The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic α-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic α-helix or in terphenyl helix mimetics.

PIPERAZINE UREA DERIVATIVES AS MELANOCORTIN-4 RECEPTOR AGONISTS

Certain novel piperazine urea derivatives are agonists of the human melanocortin-4 receptor (MC-4R) and, in particular, are receptor-subtype selective agonists of MC-4R. They are useful for the treatment, control, or prevention of diseases and disorders r

A novel and facile method to synthesize (R)- and (S)-2-methylpiperazine

A concise and efficient synthesis of (R)- and (S)-2-methylpiperazine in only five steps from (D)- and (L)-alanine is described. The key step is reaction of benzylamine with a bifunctional molecule to build a six-membered ring.

Anti-inflammatory piperazinyl-benzyl-tetrazole derivatives and intermediates thereof

This invention relates to tetrazoles and their pharmaceutically acceptable salts which are selective agonists for the delta opioid receptor, particularly useful in the treatment of inflammatory diseases such as arthritis, psoriasis, asthma, inflammatory bowel disease, disorders or respiratory function, gastrointestinal disorders such as functional bowel disease and functional GI disorders, of formula (I) wherein R1is H, C2-C6alkanoyl, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, (C3-C7cycloalkyl)-(C1-C4alkyl), (C1-C4alkoxy)-(C1-C4alkyl), carboxy-(C1-C4alkyl), aryl-(C1-C4alkyl) or heteroaryl-(C1-C4alkyl); R2and R3are each independently H or C1-C4alkyl; R4is selected from (i) H, (ii) a group of the formula R6—(CH2)m—Z—(CH2)n—, where m is 0, 1, 2 or 3, n is 1, 2 or 3, Z is a direct link or O, and R6is —CO2H or —CO2(C1-C4alkyl), and (iii) a group of formula (a) where R7is H or C1-C4alkyl; and R5is hydroxy, C1-C4alkoxy or —NHSO2(C1-C4alkyl); with the proviso that when Z is O, m is 1, 2 or 3 and n is 2 or 3.

Exploring the structure-activity relationships of [1-(4-(4- tert-butyl-3'-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), a high-affinity and selective δ-opioid receptor nonpeptide agonist ligand

SL-3111 [1-(4-tert-butyl-3'-hydroxy)benzhydryl-4- benzylpiperazine] is a de novo designed, high-affinity and selective nonpeptide peptidomimetic agonist of the δ-opioid receptor. In a previous report we had described the unique biological characteristics of this ligand and also a need for further structural evaluation. To pursue this, we have introduced a completely different heterocyclic template (2 and 3), which, based on molecular modeling studies, may present the required structural features to properly orient the pharmacophore groups. We also have made more subtle changes to the original piperazine scaffold (5 and 11). The biological activities of these compounds revealed an important participation of the scaffold in the ligand-receptor interaction. To further explore functional diversity on the scaffold, we have maintained the original piperazine ring and introduced four different functionalities at position 2 of the heterocyclic ring (15a-d; a = CH2-O-CH2-Ph; b = Me; c = CH2Ph; d = CH2OH). The biological activities observed for these compounds showed a very interesting trend in terms of the steric effects of the groups introduced at this position. A decrease of almost 2000-fold in affinity and potency at the δ- receptor was observed for 15c compared with 15b. This difference may be explained if we postulate that the bioactive conformation of these peptidomimetics is close to the minimal energy conformations calculated in our study. On the basis of these findings we have realized the importance of this position to further explore and simplify the structure of future generations of peptidomimetic ligands.

Asymmetric Synthesis of 2,6-Methylated Piperazines

The complete series of enantiopure 2,6-methylated piperazines was synthesized utilizing two alternative reactions in the key bond-forming step.The dimethyl enantiomers, (2R,6R)- and (2S,6S)-2,6-dimethylpiperazine (1, 2), were prepared using either a diastereoselective triflate alkylation or a novel intermolecular Mitsunobu reaction to set the required stereochemistry.The monomethyl derivatives, (R)- and (S)-tert-butyl 2-methyl-1-piperazinecarboxylate (3, 4) were also synthesized employing the Mitsunobu cyclization strategy while the trimethyl compounds, (R)- and (S)-2,2,6- trimethylpiperazine (5, 6) were prepared using an enantiospecific triflate alkylation as the principal reaction.These methods represent efficient, general strategies for preparing a variety of 2,6-methylated piperazines for which the absolute stereochemistry can be readily controlled.