17751-47-2

Upstream product

• 110-91-8 morpholine 
• 500-22-1 3-pyridinecarboxaldehyde 
• 100-55-0 3-hydroxymethylpyridin 
• 6959-48-4 3-chloromethylpyridinium chloride 
• 626-60-8 3-Chloropyridine 
• 1268340-94-8 (morpholinium-4-ylmethyl)trifluoroborate internal salt 
• 109-02-4 4-methyl-morpholine 
• 626-55-1 3-Bromopyridine 
• 5625-90-1 4-(morpholinomethyl)morpholine 
• 3731-52-0 3-Aminomethylpyridine 

Relevant academic research and scientific papers

Synthesis of 3-(aminomethyl)pyridine by traceless C3-selective umpolung of 1-amidopyridin-1-ium salts

A natural product inspired rapid access of 3-(aminomethyl)pyridine by one-pot reaction of 1-amidopyridin-1-ium salt with aminal followed by reductive cleavage of the N-N bond is developed. This C3-selective formal C-H activation of pyridine features a traceless umpolung of the 1-amidopyridin-1-ium salt toward a Mannich type C-C bond formation of the in situ generated 1-amido-2-dialkylamino-1,2-dihydropyridine intermediate.

Palladium-Catalyzed Benzylic C-H Arylation of Azaarylmethylamines

A direct C-H functionalization approach to produce aryl(azaaryl)methylamines from azaarylmethylamines without directing groups is described. Under conditions where the azaarylmethylamines' C-H is reversibly deprotonated, a Pd(OAc)2/NIXANTPHOS-b

Regioselective borylation of the C-H bonds in alkylamines and alkyl ethers. Observation and origin of high reactivity of primary C-H bonds beta to nitrogen and oxygen

Borylation of aliphatic C-H bonds in alkylamines and alkyl ethers to form primary aminoalkyl and alkoxyalkyl boronate esters and studies on the origin of the regioselectivity of these reactions are reported. The products of these reactions can be used directly in Suzuki-Miyaura cross-coupling reactions or isolated as air-stable potassium trifluoroborate salts. Selective borylation of the terminal C-H bond at the positions β to oxygen and nitrogen occurs in preference to borylation of the other terminal C-H bonds. Experimental studies and computational results show that C-H bond cleavage is the rate-determining step of the current borylation reactions. The observed higher reactivity of C-H bonds at the terminal position of ethylamines and ethers results from a combination of attractive Lewis acid-base and hydrogen-bonding interactions, as well as typical repulsive steric interactions, in the transition state. In this transition state, the heteroatom lies directly above the boron atom of one boryl ligand, creating a stabilizing interaction between the weak Lewis acid and Lewis base, and a series of C-H bonds of the substrate lie near the oxygen atoms of the boryl ligands, participating in a set of weak C- H···O interactions that lead to significant stabilization of the transition state forming the major product.

Reinvestigation of aminomethyltrifluoroborates and their application in suzuki-miyaura cross-coupling reactions

A reinvestigation into the chemical composition of potassium aminomethyltrifluoroborates is reported. These trifluoroborato salts have been reassigned as zwitterionic ammoniomethyltrifluoroborates. Minor adjustments to the previously disclosed reaction conditions are reported that permit a similar level of activity as nucleophiles in Suzuki-Miyaura cross-coupling reactions.

Selective cross-coupling of amines by alumina-supported palladium nanocluster catalysts

Al2O3-supported Pd nanoclusters with an average particle size of 1.8 nm act as a reusable catalyst for the selective cross-coupling of amines. The reaction is a structure-sensitive reaction, demanding coordinatively unsaturated Pd atoms on a metallic nanocluster. The support also affects the activity, an amphoteric oxide (Al2O 3) is most effective. The Royal Society of Chemistry.

Use of polymer supported reagents for clean multi-step organic synthesis: Preparation of amines and amine derivatives from alcohols for use in compound library generation

The automated sequential application of polymer supported perruthenate (PSP) and polymer supported cyanoborohydride (PSCBH) in an oxidation-reductive amination procedure allowed the efficient transformation of simple alcohols into more complex amines which can be further derivatised by the use of polymer bound amino sulfonylpyridinium chlorides.

Anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory 1-[(benzoylphenyl)-lower-alkyl]piperidines and analogs thereof

1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH2)n --N=B]-substituted-piperidines, useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate subs

Benzoylphenyl lower alkanoyl piperidines

1-[(3- or 4-Benzoylphenyl)-lower-alkyl]-[(CH2)n -N=B]-substituted-piperidines, useful as anti-asthmatic, anti-allergic, anti-cholinergic, bronchodilator and anti-inflammatory agents, are prepared by alkylation of an appropriate subst