3433-38-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Bromomethyl-piperidine is used as a key intermediate for the production of various drugs, including antihistamines and antipsychotics, due to its ability to facilitate the synthesis of these medications.
Used in Organic Synthesis:
2-Bromomethyl-piperidine is used as a reagent in organic synthesis, particularly for the preparation of heterocyclic compounds, which are essential in the development of new chemical entities with potential applications in various fields.
Safety Precautions:
2-Bromomethyl-piperidine is known to be a skin and eye irritant and can be harmful if inhaled or ingested. Therefore, it is crucial to take proper safety precautions when handling 2-Bromomethyl-piperidine to minimize health risks.

Upstream product

• 3433-37-2 piperidin-2-ylmethanol 

Downstream Products

• 1390625-58-7 2-((dicyclohexylphosphino)methyl)piperidine-diborane complex 
• 1431693-89-8 dicyclohexyl(piperidin-2-ylmethyl)phosphine oxide 

Relevant academic research and scientific papers

Catalytic hydrogenation of unactivated amides enabled by hydrogenation of catalyst precursor

A general method for catalytic hydrogenation of unactivated amides was achieved. During the catalyst induction period, a novel structural change was observed involving full hydrogenation of the interior unsaturated bonds of the pyridines of the Ru-containing catalyst precursor. Based on this observation, the mechanism of amide hydrogenation may involve a two-step pathway, wherein the Ru catalyst having an H-Ru-N-H functionality is generated in the first step, followed by the amide carbonyl group interacting with the outer, rather than the inner, sphere of the Ru catalyst.

Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)-piperidine to alkyl acrylates: Application towards the synthesis of 2-(methoxycarbonyl) indolizidine

Conjugate addition of 2-(bromomethyl)- and 2-(2-bromoethyl)piperidine hydrobromide to methyl and ethyl acrylate in the presence of triethylamine afforded the corresponding 3-[2-(bromomethyl)piperidin-1-yl]propanoates and 3-[2-(2-bromoethyl)piperidin-1-yl]propanoates for the first time. Furthermore, methyl 3-[2-(bromomethyl)piperidin-1-yl]propanoate was converted into the novel 2-(methoxycarbonyl)indolizidine upon treatment with lithium diisopropylamide in THF. The latter ester was easily reduced by means of lithium aluminium hydride in diethyl ether, affording 2-(hydroxymethyl)indolizidine in high yield.

Bicyclic β-sultams: Synthesis from monocyclic β-aminothiols and some properties

The cyclamine methanethiols 7 are prepared from the corresponding alcohols 3 and oxidatively transformed by treatment with chlorine into the cyclic substituted taurinechlorides 8. Upon treatment with bases, 8 is cyclized yielding the bicyclic β-sultams 9. Some spectroscopic properties and the solvolysis of 9 are briefly discussed.