31637-11-3

Usage

Class

Piperidine class of compounds

Derivative of

Pipercolic acid

Biological Significance

Important component of various biologically active molecules

Potential Applications

Medicine and pharmacology

Properties

Neuroprotective and analgesic properties

Use

Building block in the synthesis of other organic compounds

Structure

Contains a phenyl ring and a piperidine ring

Chemical Properties

Unique due to its structure, suitable for various applications in the chemical and pharmaceutical industries

Upstream product

• 19099-93-5 benzyl 4-oxo-1-piperidinecarboxylate 
• 100-59-4 phenylmagnesium chloride 
• 95798-23-5 1-(benzyloxycarbonyl)-4-hydroxypiperidine 
• 40807-61-2 4-hydroxy-4-phenylpiperidin 
• 501-53-1 benzyl chloroformate 
• 108-86-1 bromobenzene 
• 5382-16-1 4-HYDROXYPIPERIDINE 

Downstream Products

• 161609-91-2 benzyl 4-phenyl-3,6-dihydropyridine-1(2H)-carboxylate 
• 871926-93-1 3-formyl-3-phenyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 871926-94-2 3,4-dihydroxy-4-phenyl-piperidine-1-carboxylic acid benzyl ester 
• 871926-95-3 1-((benzyloxy)carbonyl)-3-phenylpyrrolidine-3-carboxylic acid 
• 871927-01-4 3-benzyloxy-1-benzyloxycarbonyl-4-hydroxy-4-phenyl piperidine 
• 1027057-30-2 3-benzylcarbamoyl-3-phenyl-pyrrolidine-1-carboxylic acid benzyl ester 
• 871926-92-0 1-benzyl-2-oxo-1,2-dihydro-spiro[indole-3,3'-pyrrolidine]-1'-carboxylic acid benzyl ester 

Relevant academic research and scientific papers

Catalytic Friedel-Crafts Reactions on Saturated Heterocycles and Small Rings for sp3-sp2 Coupling of Medicinally Relevant Fragments

gem-Diarylheterocycles display a wide range of biological activity. Here we present a systematic study into the formation of 4- to 6-membered O- and N-heterocycles and cyclobutanes bearing the diaryl motif through a catalytic Friedel–Crafts reaction from the corresponding benzylic alcohols. 3,3-Diaryltetrahydrofurans, 4,4-diaryltetrahydropyrans, 3,3-diarylpyrrolidines, 4,4-diaryl-piperidines, as well as diarylcyclobutanes are examined, with results for 3,3-diaryloxetanes and 3,3-diarylazetidines presented for comparison. Three catalytic systems are investigated for each substrate [Ca(II), Li(I) and Fe(III)], across preinstalled aromatic groups of differing electronic character. In most cases examined, the diaryl product is obtained directly from the alcohol with good yields using the most appropriate catalyst system. In the absence of a nucleophile, the olefins from the 5- and 6-membered substrates by elimination of water are obtained under the same reaction conditions.

Synthesis of (±)-coerulescine and a formal synthesis of (±)-horsfiline

A straightforward synthesis of (±)-coerulescine and (±)-horsfiline has been established from 3-formyl-3-phenylpyrrolidine employing 4-hydroxypiperidine as the starting material. There are two remarkable steps for the synthesis of (±)-coerulescine and (±)-horsfiline. One is the rapid access to produce 3-formyl-3-phenylpyrrolidine by Lewis acid-catalyzed rearrangement of 3,4-dihydroxy-4-phenylpiperidine. The other key step is an intramolecular electrophilic cyclization from 3-benzylcarbamoyl-3- phenylpyrrolidine to the 3,3-spirocyclic 2-oxindole ring skeleton.

Aryl substituted heterocycles

The present invention concerns the novel use of aryl substituted heterocycles of formula I, set out below, which antagonize the pharmacological actions of one of ent endogenous neuropeptide tachykinins an the neurokinin 2 (NK2) receptor making them useful whenever such antagonism is desired, such as in the treatment of asthma and related conditions. The invention also provides pharmaceutical compositions containing the aryl substituted heterocycles for use in such treatment. Certain novel aryl substituted heterocycles of formula I and novel intermediates for their manufacture are also provided. STR1