4452-12-4

Usage

Chemical Family

Arylpiperidines

Physical Description

White to light yellow crystalline solid with a faint odor

Usage

Intermediate in the synthesis of pharmaceuticals and organic compounds

Potential Applications

Medicinal chemistry, therapeutic agent for various medical conditions

Biological and Pharmacological Effects

Not fully elucidated, requires further research for full understanding.

Upstream product

• 98-86-2 acetophenone 
• 3592-47-0 Benzaldehyde-d 
• 110-89-4 piperidine 
• 70485-98-2 (E)-3-(diisopropylamino)-1-phenylprop-2-en-1-one 
• 100-52-7 benzaldehyde 
• 51752-63-7 Piperidineformaldehyde diethylacetal 
• 49660-41-5 triethyl-(3-oxo-3-phenyl-propenyl)-ammonium; chloride 
• 120225-40-3 trimethyl-(3-oxo-3-phenyl-propenyl)-ammonium; chloride 
• 21440-46-0 1-Phenyl-3-p-toluolsulfonyl-propen-⁽²⁾-on-⁽¹⁾ 
• 40685-20-9 (E)-3-methoxy-1-phenylprop-2-en-1-one 

Downstream Products

• 62035-05-6 5-benzoyl-2-phenyl-6-piperidin-1-yl-5,6-dihydro-[1,3]thiazin-4-one 
• 62035-04-5 5-benzoyl-2-phenyl-[1,3]thiazin-4-one 
• 7632-73-7 1-phenyl-3-piperidino-2-propene-1-thione 
• 92126-72-2 6-phenyl-2-thioxo-1,2-dihydropyridine-3-carbonitrile 
• 99482-90-3 4-phenyl-3-cyano-2(1H)-pyridinethione 
• 118947-88-9 6-Phenyl-2-selenoxo-1,2-dihydro-pyridine-3-carbonitrile 
• 99482-91-4 4-phenyl-3-cyano-2(1H)-pyridineselenone 
• 2305-87-5 4-phenylpyrimidin-2-amine 
• 99482-93-6 3-amino-2-benzoyl-4-phenylthieno<2,3-b>pyridine 
• 1702-14-3 ethyl 2-methyl-6-phenylnicotinate 
• 58861-75-9 1‐phenyl‐2‐(piperidin‐1‐yl)‐2‐thioxoethan‐1‐one 
• 14377-63-0 1-(phenylglyoxylyl)piperidine 

Relevant academic research and scientific papers

Scalable synthesis of enaminones utilizing Gold's reagents

Several Gold's reagents were synthesized from cyanuric chloride and N,N-dialkylformamides. These synthetic equivalents of N,N-dimethylformamide dimethyl acetal were used in an optimized and scalable procedure for the regioselective synthesis of a variety

Acetylide Ion (C22-) as a synthon to link electrophiles and nucleophiles: A simple method for enaminone synthesis

Friendly competition: A three-component reaction system composed of calcium carbide, an aryl aldehyde, and an amine gave enaminones or propargylamines (see picture) in a predictable manner through competitive pathways. The system enables the cost-efficient synthesis of a variety of enaminones from readily accessible small molecules and demonstrates the versatility of the acetylide ion, which can be used to bridge electrophiles and nucleophiles. Copyright

Synthesis of propyne iminium triflates by vacuum thermolysis of 3- trifloxypropene iminium triflates: Scope and some limitations

Vacuum thermolysis of various 3-trifloxypropene iminium triflates 1 leads to propyne iminium triflates 2 by β-elimination of triflic acid. In contrast, salt 1j undergoes an intramolecular aromatic S(E) reaction.

AMINOLYSIS OF VINYLAMMONIUM SALTS. EFFECTS OF STRUCTURE AND MEDIUM

The kinetics of the aminolysis of a series of vinylammonium salts ZCH=CHN+R3*X- were investigated in polar solvents and in water at 25 deg C.A quantitative assessment was made of the effect of the nature of the medium and the structure of activating group Z on the rate of the investigated processes.The aminolysis rate of the salts increases with increase in the donating characteristics of the solvent on account of the greater stabilization of the transition state compared with the initial state.Increase in the accepting characteristics of the medium leads to retardation of the process as a result of increase in the electrophilic solvation of the amine in the initial state.

Cation-Anion Combination Reactions. 20. Reactions of Nucleophiles with trans-3-Methoxy- and trans-3-(Methylthio)acrylophenones

The reactions of a number of nucleophiles with trans-3-methoxyacrylophenone (MeOAcr) and with trans-3-(methylthio)acrylophenone (MeSAcr) in water and methanol have been studied.The reactions of amines produce enamines as the first observable products, and primary amines show simple kinetics: first-order with respect to amine and first-order with respect to the acrylophenone.Piperidine reactions show kinetics which are consistent with a change in the rate-determining step with a change in amine concentration.Methoxylamine reactions produce the monooximes, and semicarbazide reactions produce the monosemicarbazone with MeOAcr but the disemicarbazone with MeSAcr.The reactions of hydroxide ion produced the enolate of benzoylacetaldehyde, which, at the high base concentration used in the MeSAcr reaction, was further converted to acetophenone and formate ion.Methoxide and cyanide ion reactions given addition across the double bond.Rate constants for the reactions of MeOAcr are 20-1000 times greater than those for corresponding reactions of MeSAcr.There is a very good correlation of the rate constants for reactions of nucleophiles with MeOAcr and those with 2,4-dinitrophenyl acetate in both water and methanol solution.

Reactions of &α,&β-Unsaturated &γ-Oxosulfones with Nucleophiles

Bromination of the γ-oxosulfones 1 and subsequent dehydrohalogenation leads to the α,β-unsaturated γ-oxosulfones 3.These products react with primary and secondary amines to yield the enaminoketones 7. γ-Oxobissulfones 10 are formed from 3 by addition of t