145508-94-7

Basic information

• Product Name: 1-Boc-4-iodomethyl-piperidine
• Synonyms: 1-TERT-BUTOXYCARBONYL-4-(IODOMETHYL)PIPERIDINE;1-Boc-4-iodomethylpiperidine;tert-butyl 4-(iodomethyl)piperidine-1-carboxylate
• CAS NO: 145508-94-7
• Molecular Formula: C₁₁H₂₀INO₂
• Molecular Weight: 325.19
• Product Categories: pharmacetical
• Mol File: 145508-94-7.mol
• Article Data: 29

Chemical Properties

• Boiling Point: 336.593 °C at 760 mmHg
• Flash Point: 157.366 °C
• Appearance: /
• Density: 1.448 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: 2-8°C(protect from light)
• PKA: -1.82±0.40(Predicted)
• CAS DataBase Reference: 1-Boc-4-iodomethyl-piperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Boc-4-iodomethyl-piperidine(145508-94-7)
• EPA Substance Registry System: 1-Boc-4-iodomethyl-piperidine(145508-94-7)

Safety Data

• Hazardous Substances Data: 145508-94-7(Hazardous Substances Data)

Usage

General Description

1-Boc-4-iodomethyl-piperidine is a chemical compound, typically utilized in laboratory research or as an intermediate in the production of other substances. The term 'Boc' in its nomenclature indicates that it is a derivative of piperidine that has undergone a reaction with Boc2O, also known as Di-tert-butyl dicarbonate. This reaction results in protection of the amine group within the piperidine molecule. The 'iodomethyl' component implies the addition of a iodomethyl group at position 4 of the piperidine ring. As an iodized compound, it is also a potential precursor for further reactions such as cross-coupling. As it is a specialized chemical compound, it should be handled by trained personnel with proper safety precautions due to its potential reactivity and biologic effects.

InChI:InChI=1/C11H20INO2/c1-11(2,3)15-10(14)13-6-4-9(8-12)5-7-13/h9H,4-8H2,1-3H3

Upstream product

• 123855-51-6 tert-butyl 4-(hydroxymethyl)piperidin-1-carboxylate 
• 158407-04-6 tert-butyl 4-(bromomethyl)piperidine-1-carboxylate 
• 6457-49-4 4-piperidinemethanol 
• 84358-13-4 N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid 
• 157688-46-5 2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid 
• 141699-59-4 1-(tert-butoxycarbonyl)piperidin-4-yl methanesulfonate 
• 161975-39-9 tert-butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 142851-03-4 1-tert-butyl 4-ethyl piperidine-1,4-dicarboxylate 
• 1126-09-6 4-carbethoxypiperidine 

Downstream Products

• 321328-47-6 tert-butyl 4-(2-((diphenylmethylene)amino)-3-ethoxy-3-oxopropyl)piperidine-1-carboxylate 
• 652130-41-1 1-t-BOC-[4-((5,6-dimethoxy-2-methoxycarbonylindan-1-on)-2yl)methyl]piperidine 
• 956519-39-4 tert-butyl 4-{2-[7-(tert-butyldimethylsilanyloxymethyl)-6-(4-fluorobenzyloxy)benz[d]isoxazol-3-yl]ethyl}piperidine-1-carboxylate 
• 251107-37-6 1-t-butyloxycarbonyl-4-benzylpiperidine 

Relevant articles and documents

Selective acetylcholinesterase inhibitors derived from muscle relaxant dantrolene

Dantrolene, the only therapeutic agent for malignant hyperthermia, is known to have not only a muscle relaxant effect, but also a neuroprotective effect and Alzheimer's disease improving effect. Recently, it has been reported that dantrolene has a weak inhibitory effect on acetylcholinesterase (AChE), which is a therapeutic drug target for Alzheimer's disease. Thus, we focused on developing of AChE inhibitors with benzylpiperidine/piperazine moieties that are based on the dantrolene skeleton. Several derivatives showed an inhibitory activity. Among them, ortho-nitro derivative 8c showed the most potent inhibitory activity with the IC50 value of 34.2 nM. Furthermore, Lineweaver-Burk plot analysis indicated that 8c is AChE-selective inhibitor, which shows only a weak inhibitory effect on butyrylcholinesterase (BuChE) and a non-competitive inhibition.

Design of iodinated radioligands for SPECT imaging of central human 5-HT4R using a ligand lipophilicity efficiency approach

A series of iodinated ligands for the SPECT imaging of 5-HT4 receptors was designed starting from the previously reported hit MR-26132. We focused on the modulation of the piperidine-containing lateral chain by introducing hydrophilic groups in order to decrease the liphophilicity of the new ligands. All the synthesized compounds were tested for their binding affinities on 5-HT4Rs and based on the Ligand Lipophilicity Efficiency approach, compound 13 was further selected for radioiodination with iodine-125 and imaging experiments. Compound 13 showed its ability to displace the specific signal of the reference compound [125I]SB-207710 but no significant detection of [125I]13 was observed in vivo in SPECT experiments.

Novel multitarget-directed ligands targeting acetylcholinesterase and σ1 receptors as lead compounds for treatment of Alzheimer's disease: Synthesis, evaluation, and structural characterization of their complexes with acetylcholinesterase

Pleiotropic intervention may be a requirement for effective limitation of the progression of multifactorial diseases such as Alzheimer's Disease. One approach to such intervention is to design a single chemical entity capable of acting on two or more targets of interest, which are accordingly known as Multi-Target Directed Ligands (MTDLs). We recently described donecopride, the first MTDL able to simultaneously inhibit acetylcholinesterase and act as an agonist of the 5-HT4 receptor, which displays promising activities in vivo. Pharmacomodulation of donecopride allowed us to develop a novel series of indole derivatives possessing interesting in vitro activities toward AChE and the σ1 receptor. The crystal structures of complexes of the most promising compounds with Torpedo californica AChE were solved in order to further understand their mode of inhibition.