53788-49-1

Basic information

• Product Name: 1-Boc-4-methylpiperazine
• Synonyms: 1-BOC-4-METHYLPIPERAZINE;4-METHYL-PIPERAZINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER;1-Methyl-4-(tert-butoxycarbonyl)piperazine;4-Methyl-1-piperazinecarboxylic Acid 1,1-Dimethylethyl Ester;N-Boc-N-methylpiperazine;4-Methyl-1-piperazinecarboxylic Acid 1,1-DiMethylethyl Ester-d3;4-Methylpiperazine-1-carboxylic Acid tert-Butyl Ester-d3;N-Boc-N-Methylpiperazine-d3
• CAS NO: 53788-49-1
• Molecular Formula: C₁₀H₂₀N₂O₂
• Molecular Weight: 200.28
• Product Categories: Piperidines, Piperidones, Piperazines;Heterocyclic Compounds;Heterocycles;Intermediates
• Mol File: 53788-49-1.mol

Chemical Properties

• Boiling Point: 254.8 °C at 760 mmHg
• Flash Point: 107.9 °C
• Appearance: /
• Density: 1.023 g/cm³
• Vapor Pressure: 0.0169mmHg at 25°C
• Refractive Index: 1.474
• Storage Temp.: 2-8°C
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate, Methanol
• PKA: 6.90±0.10(Predicted)
• CAS DataBase Reference: 1-Boc-4-methylpiperazine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-methylpiperazine(53788-49-1)
• EPA Substance Registry System: 1-Boc-4-methylpiperazine(53788-49-1)

Safety Data

• Hazardous Substances Data: 53788-49-1(Hazardous Substances Data)

Usage

Uses

1-Boc-4-methylpiperazine is used as a synthetic intermediate for the preparation of various pharmaceutical compounds and bioactive molecules. Its primary application is in the synthesis of piperazine-1-carboxamide derivatives, which are known as fatty acid amide hydrolase (FAAH) inhibitors. FAAH inhibitors have potential therapeutic applications in the treatment of various neurological disorders, such as anxiety, depression, and chronic pain.
Used in Pharmaceutical Industry:
1-Boc-4-methylpiperazine is used as a key building block for the synthesis of FAAH inhibitors. These inhibitors are being investigated for their potential therapeutic effects in treating neurological disorders. By inhibiting FAAH, these compounds can modulate the endocannabinoid system, which plays a crucial role in regulating various physiological processes, including mood, appetite, and pain perception.
Used in Chemical Research:
1-Boc-4-methylpiperazine is also utilized as a valuable research tool in the field of organic chemistry. Its unique structural features and reactivity make it an attractive candidate for the development of new synthetic methods and strategies. Researchers can use 1-Boc-4-methylpiperazine to explore novel reaction pathways, optimize reaction conditions, and develop more efficient and selective synthetic routes to target molecules.

InChI:InChI=1/C10H20N2O2/c1-10(2,3)14-9(13)12-7-5-11(4)6-8-12/h5-8H2,1-4H3

Upstream product

• 74-83-9 methyl bromide 
• 57260-71-6 1-t-Butoxycarbonylpiperazine 
• 109-01-3 1-methyl-piperazine 
• 201230-82-2 carbon monoxide 
• 75-65-0 tert-butyl alcohol 
• 183383-30-4 tert-butyl 4-formylpiperazine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 870-46-2 t-butoxycarbonylhydrazine 
• 1070-19-5 N-(tert-butyloxycarbonyl) azide 

Downstream Products

• 1007315-07-2 4-t-boc-1-methyl-1-(4-nitrophenyl)piperazinium fluoride 
• 313657-11-3 (2R)-Methyl-1-[3-(2-phenoxyethoxy)-2-pyrazinyl]piperazine, Hydrochloride 
• 1484327-92-5 tert-butyl 2-(4-methylpiperazin-1-yl)ethylcarbamate 
• 479691-64-0 4-[4-(3-chloro-benzylamino)-pyrimidin-2-yl]-piperazine-1-carboxylic acid tert-butyl ester 
• 479691-43-5 4-{4-[1-(2-chloro-phenyl)-ethoxy]-pyrimidin-2-yl}-piperazine-1-carboxylic acid tert-butyl ester 
• 479691-44-6 4-[1-(2-Chloro-phenyl)-ethoxy]-2-piperazin-1-yl-pyrimidine 
• 1143578-98-6 4-[4-(3,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide 
• 1143578-94-2 4-[4-(3,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide 
• 1143578-90-8 4-[4-(2,5-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide 
• 1143577-36-9 4-[4-(2,4-difluorophenyl)pyrimidin-2-yl]-N-(pyridazin-3-yl)piperazine-1-carboxamide 
• 1143623-67-9 4-(3,5-Difluorophenyl)-2-(piperazin-1-yl)pyrimidine 
• 1143623-66-8 4-(3,4-difluorophenyl)-2-(piperazin-1-yl)pyrimidine dihydrochloride 
• 1143623-65-7 4-(2,5-difluorophenyl)-2-(piperazin-1-yl)pyrimidine 
• 1143577-34-7 4-(2,4-difluorophenyl)-2-(piperazin-1-yl)pyrimidine 

Relevant articles and documents

Design, Synthesis, and Bioevaluation of 2-Aminopteridin-7(8H)-one Derivatives as Novel Potent Adenosine A2A Receptor Antagonists for Cancer Immunotherapy

In recent years, the adenosine A2A receptor (A2AR) has shown exciting progress in the development of immunotherapies for the treatment of cancer. Herein, a 2-amino-7,9-dihydro-8H-purin-8-one compound (1) was identified as an A2AR antagonist hit through in-house library screening. Extensive structure-activity relationship (SAR) studies led to the discovery of 2-aminopteridin-7(8H)-one derivatives, which showed high potencies on A2AR in the cAMP assay. Compound 57 stood out with an IC50 value of 8.3 ± 0.4 nM against A2AR at the 5′-N-ethylcarboxamidoadenosine (NECA) level of 40 nM. The antagonistic effect of 57 was sustained even at a higher NECA concentration of 1 μM, which mimicked the adenosine level in the tumor microenvironment (TME). Importantly, 57 enhanced T cell activation in both the IL-2 production assay and the cancer-cell-killing model, thus demonstrating its potential as a lead for developing novel A2AR antagonists in cancer immunotherapy.

Sustainable Route Toward N-Boc Amines: AuCl3/CuI-Catalyzed N-tert-butyloxycarbonylation of Amines at Room Temperature

N-tert-butoxycarbonyl (N-Boc) amines are useful intermediates in synthetic/medicinal chemistry. Traditionally, they are prepared via an indirect phosgene route with poor atom economy. Herein, a step- and atom-economic synthesis of N-Boc amines from amines, t-butanol, and CO was reported at room temperature. Notably, this N-tert-butyloxycarbonylation procedure utilized ready-made substrates, commercially available AuCl3/CuI as catalysts, and O2 from air as the sole oxidant. This catalytic system provided unique selectivity for N-Boc amines in good yields. More significantly, gram-scale preparation of medicinally important N-Boc amine intermediates was successfully implement, which demonstrated a potential application prospect in industrial syntheses. Furthermore, this approach also showed good compatibility with tertiary and other useful alcohols. Investigations of the mechanisms revealed that gold catalyzed the reaction and copper acted as electron transfer mediator in the catalytic cycle.

[TPA][Pro] ionic liquid as efficient reaction medium for N-tert-Boc protection of amines

A facile and efficient N-tert-Boc protection of amines is described by the reaction of various primary, secondary, benzylic and aryl amines with di-tert-butyl dicarbonate in the ionic liquid [TPA][Pro] at room temperature. All the N-tert-butylcarbamates are afforded in excellent yields. A catalyst-free method was developed and the ionic liquid [TPA][Pro] can be recovered and reused for several times without loss of its activity.

General Procedures for the Lithiation/Trapping of N-Boc Piperazines

To provide α-substituted piperazines for early stage medicinal chemistry studies, a simple, general synthetic approach is required. Here, we report the development of two general and simple procedures for the racemic lithiation/trapping of N-Boc piperazin

Chelating Bis(1,2,3-triazol-5-ylidene) Rhodium Complexes: Versatile Catalysts for Hydrosilylation Reactions

NHC-rhodium complexes (NHC=N-heterocyclic carbenes) have been widely used as efficient catalysts for hydrosilylation reactions. However, the substrates were mostly limited to reactive carbonyl compounds (aldehydes and ketones) or carbon-carbon multiple bonds. Here, we describe the application of newly-developed chelating bis(tzNHC)-rhodium complexes (tz=1,2,3-triazol-5-ylidene) for several reductive transformations. With these catalysts, the formal reductive methylation of amines using carbon dioxide, the hydrosilylation of amides and carboxylic acids, and the reductive alkylation of amines using carboxylic acids have been achieved under mild reaction conditions.

NOVEL CEPHEM COMPOUND HAVING CATECHOL OR PSEUDO-CATECHOL STRUCTURE

The present invention provides a novel compound which has a wide antimicrobial spectrum, and in particular exhibits potent antimicrobial activity against beta-lactamase producing Gram negative bacteria. Specifically, the present invention provides a compound of the formula (I): wherein each symbol is as defined in the specification, or an amino-protected compound when the amino group is present on the ring in the 7-side chain, or a pharmaceutically acceptable salt thereof, and a pharmaceutical composition comprising the same.

HETEROCYCLIC COMPOUND

Provided is a compound useful for the prophylaxis or treatment of cancer. The present invention relates to a compound represented by formula (I): wherein each symbol in the formula is as defined in the specification, or a salt thereof or a prodrug thereof, which is useful for the prophylaxis or treatment of cancer.

Nonsolvent application of ionic liquids: Organo-catalysis by 1-alkyl-3-methylimidazolium cation based room-temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency

1-Alkyl-3-methylimidazolium cation based ionic liquids efficiently catalyze N-tert-butyloxycarbonylation of amines with excellent chemoselectivity. The catalytic role of the ionic liquid is envisaged as "electrophilic activation" of di-tert-butyl dicarbonate (Boc2O) through bifurcated hydrogen bond formation with the C-2 hydrogen of the 1-alkyl-3-methylimidazolium cation and has been supported by a downfield shift of the imidazolium C-2 hydrogen of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([bmim][NTf2]) from δ 8.39 to 8.66 in the presence of Boc2O in the 1H NMR and a drastic reduction of the catalytic efficiency with 1-butyl-2,3-dimethylimidazolium ionic liquids that are devoid of the C-2 hydrogen. The differential time required for reaction with aromatic and aliphatic amines has offered means for selective N-t-Boc formation during inter and intramolecular competitions. Preferential N-t-Boc formation with secondary aliphatic amine has been achieved in the presence of primary aliphatic amine. Comparison of the catalytic efficiency for N-t-Boc formation with a common substrate revealed that [bmim][NTf2] is superior to the reported Lewis acid catalysts.

Amberlyst-15: a mild, efficient and reusable heterogeneous catalyst for N-tert-butoxycarbonylation of amines

A mild and versatile method has been developed for the chemoselective N-tert-butoxycarbonylation of amines in the presence of Amberlyst-15 under solvent-free condition. The method is general for the preparation of N-Boc derivatives of aliphatic (acyclic and cyclic) and aromatic amines.

AMIDE COMPOUND

An object of the present invention is to provide a novel fused-ring compound which has a FAAH inhibitory effect and is useful as an analgesic. The present invention relates to a compound represented by formula (I): wherein symbols are as defined in the specification, or salt thereof.