171009-41-9

Usage

Substituted piperidine derivative

A modified version of the piperidine molecule, with one or more hydrogen atoms replaced by other functional groups (tosyl and bromo groups in this case).

Tosyl group

A tosyl group (sulfonyl group derived from toluene) is attached to the piperidine ring, providing opportunities for further functionalization and modification of the compound.

Bromine atom

A bromine atom is attached to the piperidine ring, which can be used for various chemical reactions and functionalization processes.

Building block in organic synthesis and medicinal chemistry

1-tosyl-3-bromo-piperidin-4-one is commonly used as a starting material or intermediate in the synthesis of more complex organic compounds, particularly in the development of pharmaceutical drugs.

Versatile intermediate

Due to its unique structure and reactivity, 1-tosyl-3-bromo-piperidin-4-one can be used to synthesize a wide range of organic compounds, including biologically active molecules and pharmaceuticals.

Opportunities for further functionalization and modification

The presence of the tosyl and bromo groups in 1-tosyl-3-bromo-piperidin-4-one allows for additional chemical reactions and modifications, making it a valuable tool for chemical research and drug discovery.

Upstream product

• 33439-27-9 N-tosyl-4-piperidone 
• 1332708-91-4 C₁₅H₂₃NO₃SSi 
• 98-59-9 p-toluenesulfonyl chloride 
• 41979-39-9 4-piperidone hydrochloride 

Downstream Products

• 171009-42-0 3-bromo-5-ethoxycarbonyl-1-(4'-methylphenylsulfonyl)azepan-4-one 
• 949852-44-2 5-(toluene-4-sulfonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine 
• 1509927-90-5 1-[(ethoxycarbonothioyl)thio]-2-(4-oxo-1-tosylpiperidin-3-yl)ethyl pivalate 
• 1101206-99-8 dithiocarbonic acid O-ethyl ester S-[4-oxo-1-(toluene-4-sulfonyl)-piperidin-3-yl]ester 
• 1350731-16-6 2-(4-methylphenyl)sulfonyl-1,2,3,4-tetrahydropyrido[3,4-b]quinoxaline 
• 171230-63-0 (3S,4S)-3-(4-benzyloxybenzoylamino)-4-hydroxyazepane-1-carboxylic acid benzyl ester 
• 158584-98-6 4-hydroxy-3-[4-(phenylmethoxy)benzoylamino]-1-(phenylmethoxycarbonyl)-hexahydroazepine 

Relevant academic research and scientific papers

Flexible routes to thiophenes

Three convergent routes to thiophenes are described, hinging on the radical addition of α-xanthyl ketones to ethyl vinyl sulfide or to vinyl pivalate. The latter route ultimately proved to be the most versatile and efficient (61-94%).

Synthesis of quinoxaline analogues

Substituted tricyclic or tetracyclic quinoxalines, tricyclic pyridoquinoxalines and bis-quinoxalines were synthesized in high yields starting from cyclic ketones by the -bromination of cyclic ketones with N-bromosuccinimide (NBS) followed by condensation of the resulting -bromo ketones with 1,2-diaminobenzene, 3,4-diaminopyridine, or 3,3-diaminobenzidine. Georg Thieme Verlag Stuttgart New York.

Design, synthesis, and structure-activity relationships of novel bicyclic azole-amines as negative allosteric modulators of metabotropic glutamate receptor 5

A novel series of diaryl bicyclic azole-amines that are potent selective negative modulators of metabotropic glutamate receptor 5 (mGluR5) were identified through rational design. An initial hit compound 5a of modest potency (IC50 = 1.2 μM) was synthesized. Evaluation of structure-activity relationships (SAR) on the left-hand side of the molecule revealed a preference for a 2-substituted pyridine group linked directly to the central heterocycle. Variation of the central azolo-amine portion of the molecule revealed a preference for the [4,5-c]-oxazoloazepine scaffold, while right-hand side variants showed a preference for ortho- and meta-substituted benzene rings linked directly to the tertiary amine of the saturated heterocycle. These iterations led to the synthesis of 29b, a potent (IC50 = 16 nM) and selective negative modulator that showed good brain penetrance, high receptor occupancy, and a duration of action greater than 1 h in rat when administered intraperitoneally. Formal PK studies in rat and Rhesus monkey revealed a short half-life that was attributable to high first-pass clearance.

Clean six-step synthesis of a piperidino-thiomorpholine library using polymer-supported reagents

Polymer-supported reagents and other solid sequestering agents may be used to generate a library of piperidino-thiomorpholine derivatives without any chromatographic purification steps.

Total synthesis of balanol: a potent protein kinase C inhibitor of fungal origin

The total synthesis of the fungal metabolite balanol, a potent inhibitor of protein kinase C, is described.The synthesis includes a novel synthesis of 3-amino-4-hydroxyazepanes via a directed ring expansion of 3-bromopiperidin-4-ones.