173340-23-3

Basic information

• Product Name: TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE
• Synonyms: BUTTPARK 99\06-59;TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE;tert-Butyl ((1-benzylpiperidin-4-yl)Methyl)carbaMate;tert-butyl N-[(1-benzylpiperidin-4-yl)methyl]carbamate
• CAS NO: 173340-23-3
• Molecular Formula: C₁₈H₂₈N₂O₂
• Molecular Weight: 304.43
• Mol File: 173340-23-3.mol

Chemical Properties

• Boiling Point: 415.5°Cat760mmHg
• Flash Point: 205.1°C
• Appearance: /
• Density: 1.043g/cm³
• Vapor Pressure: 4.09E-07mmHg at 25°C
• Refractive Index: 1.522
• CAS DataBase Reference: TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE(CAS DataBase Reference)
• NIST Chemistry Reference: TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE(173340-23-3)
• EPA Substance Registry System: TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE(173340-23-3)

Safety Data

• Hazardous Substances Data: 173340-23-3(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE is used as a protecting group in organic synthesis for the selective protection of the N-terminus of amino acids. Its stability and ease of removal under mild acidic conditions make it a preferred choice for protecting amino groups during peptide synthesis.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE is used as a key reagent for the production of various drugs and biologically active compounds. Its ability to selectively protect amino acids during synthesis contributes to the development of new and effective medications.
Used in Peptide Synthesis:
TERT-BUTYL N-[(1-BENZYL-4-PIPERIDINYL)METHYL]CARBAMATE is used as a protecting agent in peptide synthesis to prevent unwanted side reactions and ensure the correct formation of peptide bonds. Its selective protection of the N-terminus allows for the controlled synthesis of complex peptide structures.

InChI:InChI=1/C18H28N2O2/c1-18(2,3)22-17(21)19-13-15-9-11-20(12-10-15)14-16-7-5-4-6-8-16/h4-8,15H,9-14H2,1-3H3,(H,19,21)

Upstream product

• 100-39-0 benzyl bromide 
• 135632-53-0 tert-butyl N-(4-piperidinylmethyl)carbamate 
• 100-52-7 benzaldehyde 
• 375355-32-1 1-benzoylpiperidine-4-carboxamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 88915-26-8 4-aminomethyl-1-benzylpiperidine 
• 98-88-4 benzoyl chloride 
• 39546-32-2 4-carboxamidopiperidine 

Downstream Products

• 88915-26-8 4-aminomethyl-1-benzylpiperidine 
• 135632-53-0 tert-butyl N-(4-piperidinylmethyl)carbamate 

Relevant articles and documents

Discovery and Biological Evaluation of N-Methyl-pyrrolo[2,3- b]pyridine-5-carboxamide Derivatives as JAK1-Selective Inhibitors

Janus kinase 1 (JAK1) plays a key role in most cytokine-mediated inflammatory and autoimmune responses through JAK/STAT signaling; thus, JAK1 inhibition is a promising therapeutic strategy for several diseases. Analysis of the binding modes of current JAK inhibitors to JAK isoforms allowed the design of N-alkyl-substituted 1-H-pyrrolo[2,3-b] pyridine carboxamide as a JAK1-selective scaffold, and the synthesis of various methyl amide derivatives provided 4-((cis-1-(4-chlorobenzyl)-2-methylpiperidin-4-yl)amino)-N-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxamide (31g) as a potent JAK1-selective inhibitor. In particular, the (S,S)-enantiomer of 31g (38a) exhibited excellent potency for JAK1 and selectivity over JAK2, JAK3, and TYK2. On investigating the effect of 31g on hepatic fibrosis, it was found that it reduces the proliferation and fibrogenic gene expression of TGF-β-induced hepatic stellate cells (HSCs). Specifically, 31g significantly inhibited TGF-β-induced migration of HSCs at 0.25 μM in wound-healing assays.

Claulansine F-donepezil hybrids as anti-alzheimer’s disease agents with cholinergic, free-radical scavenging, and neuroprotective activities

The multifactorial nature of Alzheimer’s disease (AD) calls for the development of multitarget agents addressing key pathogenic processes. A total of 26 Claulansine F-donepezil hybrids were designed and synthesized as multitarget drugs. Among these compounds, six compounds exhibited excellent acetylcholinesterase (AChE) inhibitory activity (half maximal inhibitory concentration (IC50) 1.63-4.62 μM). Moreover, (E)-3-(8-(tert-Butyl)-3,3-dimethyl-3,11-dihydropyrano[3,2-a]carbazol- 5-yl)-N-((1-(2-chlorobenzyl)piperidin-4-yl)methyl)acrylamide (6bd) exhibited better neuroprotective effects against OGD/R (oxygen-glucose deprivation/reoxygenation) than lead compound Claulansine F. Furthermore, 6bd could cross the blood-brain barrier in vitro. More importantly, compared to edaravone, 6bd had stronger free-radical scavenging activity. Molecular docking studies revealed that 6bd could interact with the catalytic active site of AChE. All of these outstanding in vitro results indicate 6bd as a leading structure worthy of further investigation.

Structure-based exploration and pharmacological evaluation of N-substituted piperidin-4-yl-methanamine CXCR4 chemokine receptor antagonists

Using the available structural information of the chemokine receptor CXCR4, we present hit finding and hit exploration studies that make use of virtual fragment screening, design, synthesis and structure-activity relationship (SAR) studies. Fragment 2 was identified as virtual screening hit and used as a starting point for the exploration of 31 N-substituted piperidin-4-yl-methanamine derivatives to investigate and improve the interactions with the CXCR4 binding site. Additionally, subtle structural ligand changes lead to distinct interactions with CXCR4 resulting in a full to partial displacement of CXCL12 binding and competitive and/or non-competitive antagonism. Three-dimensional quantitative structure-activity relationship (3D-QSAR) and binding model studies were used to identify important hydrophobic interactions that determine binding affinity and indicate key ligand-receptor interactions.

The Magic of Crystal Structure-Based Inhibitor Optimization: Development of a Butyrylcholinesterase Inhibitor with Picomolar Affinity and in Vivo Activity

The enzymatic activity of butyrylcholinesterase (BChE) in the brain increases with the progression of Alzheimer's disease, thus classifying BChE as a promising drug target in advanced Alzheimer's disease. We used structure-based drug discovery approaches to develop potent, selective, and reversible human BChE inhibitors. The most potent, compound 3, had a picomolar inhibition constant versus BChE due to strong cation-π interactions, as revealed by the solved crystal structure of its complex with human BChE. Additionally, compound 3 inhibits BChE ex vivo and is noncytotoxic. In vitro pharmacokinetic experiments show that compound 3 is highly protein bound, highly permeable, and metabolically stable. Finally, compound 3 crosses the blood-brain barrier, and it improves memory, cognitive functions, and learning abilities of mice in a scopolamine model of dementia. Compound 3 is thus a promising advanced lead compound for the development of drugs for alleviating symptoms of cholinergic hypofunction in patients with advanced Alzheimer's disease.

N-Propargylpiperidines with naphthalene-2-carboxamide or naphthalene-2-sulfonamide moieties: Potential multifunctional anti-Alzheimer's agents

In the brains of patients with Alzheimer's disease, the enzymatic activities of butyrylcholinesterase (BChE) and monoamine oxidase B (MAO-B) are increased. While BChE is a viable therapeutic target for alleviation of symptoms caused by cholinergic hypofunction, MAO-B is a potential therapeutic target for prevention of neurodegeneration in Alzheimer's disease. Starting with piperidine-based selective human (h)BChE inhibitors and propargylamine-based MAO inhibitors, we have designed, synthesized and biochemically evaluated a series of N-propargylpiperidines. All of these compounds inhibited hBChE with good selectivity over the related enzyme, acetylcholinesterase, and crossed the blood-brain barrier in a parallel artificial membrane permeation assay. The crystal structure of one of the inhibitors (compound 3) in complex with hBChE revealed its binding mode. Three compounds (4, 5, 6) showed concomitant inhibition of MAO-B. Additionally, the most potent hBChE inhibitor 7 and dual BChE and MAO-B inhibitor 6 were non-cytotoxic and protected neuronal SH-SY5Y cells from toxic amyloid β-peptide species.

Straightforward synthesis of orthogonally protected piperidin-3- ylmethanamine and piperidin-4-ylmethanamine derivatives

The 1,3- and 1,4-disubstituted piperidines are important building blocks in medicinal chemistry and drug discovery. We present the synthesis of orthogonally protected piperidin-3-ylmethanamine and piperidin-4-ylmethanamine derivatives from commercially available nipecotamide, isonipecotamide, nipecotic acid and isonipecotic acid. This is a straightforward two-step procedure that gives high overall yields. Purification of the intermediates using this procedure is not necessary, and the final compounds are purified by simple flash column chromatography.