18811-61-5

Usage

Chemical structure

A piperidine ring attached to a methoxymethyl group

Common use

Building block in the synthesis of various pharmaceuticals and organic compounds

Pharmacological effects

Potential ability to act as a reagent in the synthesis of novel drugs

Odor

Mild, characteristic odor

Stability

Considered to be a stable compound

Reactivity

Relatively non-reactive

Applications

Various industrial and research applications in the chemical and pharmaceutical industries

Upstream product

• 110-89-4 piperidine 
• 67-56-1 methanol 
• 50-00-0 formaldehyd 

Downstream Products

• 2905-56-8 N-Benzylpiperidine 
• 626-67-5 N-methylcyclohexylamine 
• 35278-95-6 N,N-piperidyl-1-p-tolylmethanamine 
• 4764-13-0 2-(N-piperidinylmethyl)phenol 
• 59507-42-5 1-(4-chlorobenzyl)piperidine 
• 3626-62-8 2-phenyl-1-(1-piperidinyl)ethanone 
• 19653-33-9 ethyl piperidine-1-propionate 

Relevant academic research and scientific papers

Enantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Br?nsted Acid Catalysis

The synthesis of α-aryl-β2-amino esters through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Br?nsted acid catalysis is demonstrated. The scope and limitatio

Copper-Catalyzed Oxy-aminomethylation of Diazo Compounds with N, O-Acetals

A novel oxy-aminomethylation reaction of diazo compounds has been developed, providing the α-hydroxy-β2-amino acid derivatives with quaternary carbon centers in moderate to excellent yields. Importantly, the readily available N,O-acetals have been employed as efficient bifunctionalization reagents to react with copper carbene intermediates, leading to the concurrent incorporation of an alkoxy and an iminium group into one molecule. Moreover, a water-involved three-component reaction occurs to deliver the free-hydroxy amino acid derivatives.

Copper(II)-Catalyzed [4+1] annulation of propargylamines with N,O-acetals: Entry to the synthesis of polysubstituted pyrrole derivatives

Described herein is the CuCl2-catalyzed [4+1] annulation of a variety of propargylamines with N,O-acetals that function as a C1 unit, leading to the production of polysubstituted pyrrole derivatives. Three important features of the N,O-acetal during the [4+1] annulation series via 5-endo-dig cyclization are described: an enolizable substituent adjacent to the central sp3-carbon is required, the central sp3-carbon displays the functions of both an electrophile and a nucleophile, and liberation of the secondary amine smoothly leads to the aromatization. A CuCl2-catalyzed [4+1] annulation of propargylamines with N,O-acetals having an ester, a ketone, and an amide moiety, leading to the facile preparation of polysubstituted pyrrole derivatives is presented. This annulation series was achieved through 5-endo-dig cyclization and subsequent aromatization in one pot.

Copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals under atmosphere leading to α-aryl glycine derivatives and diarylmethylamine derivatives

We demonstrated a copper(I)-catalyzed coupling reaction of aryl boronic acids with N,O-acetals and N,N-aminals leading to the synthesis of α-aryl glycines and diarylmethylamines. Under an ambient atmosphere, this catalytic system could be applied to the activation of a C(sp3)-O bond of N,O-acetals with an ester and an aryl group, or without a coordinating substituent, as well as to a C(sp3)-N bond of N,N-aminals.

N-aminomethylation vs. C-aminomethylation of indole and pyrrole with an N,O-acetal controlled by the hardness of a counter ion of an iminium compound

Under relatively strong Lewis acidic conditions (a softer counter ion) using TMSOTf and TMSI, the aminomethylation of indole or pyrrole with a typical N,O-acetal preferentially produced the kinetically favored N-aminomethylated indole or pyrrole derivative. Use of a relatively weak Lewis acid (a harder counter ion), such as TMSCl and TMSBr, preferentially produced the thermodynamically favored C-aminomethylated indole and pyrrole derivative.

Hf(OTf)4-Catalyzed regioselective N -aminomethylation of indoles and related NH-containing heterocycles

Figure presented Under Lewis acidic conditions using Hf(OTf)4, the aminomethylation of an indole derivative with a typical N,O-acetal preferentially produced kinetically favored N-aminomethylated indole derivatives instead of thermodynamically favored 3-aminomethylated indoles.

Cyanomethylamines and azidomethylamines: new general methods of the synthesis and transformations

Simple and efficient methods have been developed to obtain cyanomethylamines and azidomethylamines using reactions of methoxymethylamines with TMSCN and TMSN3, respectively. In the case of dimethylformamide dimethylacetal, only one MeO group wa