1-Phenylpiperidin-3-one

Base Information

• Chemical Name: 1-Phenylpiperidin-3-one
• CAS No.: 148494-90-0
• Molecular Formula: C11H13 N O
• Molecular Weight: 175.23
• Hs Code.: 2933399090
• Mol file: 148494-90-0.mol

Synonyms:1-Phenyl-3-piperidinone

Chemical Property of 1-Phenylpiperidin-3-one

Chemical Property:

• Vapor Pressure: 0.001mmHg at 25°C
• Boiling Point: 313 ºC
• Flash Point: 124 ºC
• PSA: 20.31000
• Density: 1.107
• LogP: 1.92090
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

1-Phenylpiperidin-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1-Phenylpiperidin-3-one is used in the synthetic preparation of lipoxygenase inhibition structure.

Technology Process of 1-Phenylpiperidin-3-one

There total 7 articles about 1-Phenylpiperidin-3-one which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 57.0%

C13H19NO2 → (2S)-phenyl-3-piperidone (148494-90-0)

Guidance literature:

With hydrogenchloride; In tert-butyl methyl ether; water; for 168h;

DOI:10.1021/acs.orglett.7b00344

Reference yield:

3-oxo-piperidine-1-carboxylic acid tert-butyl ester (98977-36-7) → (2S)-phenyl-3-piperidone (148494-90-0)

Guidance literature:

Multi-step reaction with 3 steps

1: methanesulfonic acid / 20 - 50 °C

2: tri tert-butylphosphoniumtetrafluoroborate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; potassium tert-butylate / toluene / 24 h / 100 °C / Schlenk technique

3: hydrogenchloride / water; tert-butyl methyl ether / 168 h

With hydrogenchloride; methanesulfonic acid; potassium tert-butylate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; In tert-butyl methyl ether; water; toluene;

DOI:10.1021/acs.orglett.7b00344

Reference yield:

3,3-dimethoxypiperidine (765962-69-4) → (2S)-phenyl-3-piperidone (148494-90-0)

Guidance literature:

Multi-step reaction with 2 steps

1: tri tert-butylphosphoniumtetrafluoroborate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; potassium tert-butylate / toluene / 24 h / 100 °C / Schlenk technique

2: hydrogenchloride / water; tert-butyl methyl ether / 168 h

With hydrogenchloride; potassium tert-butylate; bis(dibenzylideneacetone)-palladium⁽⁰⁾; tri tert-butylphosphoniumtetrafluoroborate; In tert-butyl methyl ether; water; toluene;

DOI:10.1021/acs.orglett.7b00344

upstream raw materials:

4-(N-ethoxycarbonylmethyl-anilino)-butyric acid ethyl ester

4-(phenylamino)butyronitrile

ethyl N-(3-cyanopropyl)-N-phenylglycinate

aniline

Downstream raw materials:

(+/-)-2-methyl-1-phenylpyrrolidine

Refernces

Biomass derived furfural-based facile synthesis of protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs

10.1039/c4cc02645d

The study presents an efficient synthetic route to produce tosyl-protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs, from biomass-derived furfural. Furfural, a platform chemical derived from agricultural waste like rice straw, is transformed into the piperidone core structure through a series of reactions involving 4-methylbenzenesulfonamide, a Lewis acid catalyst, and a rhodium-catalyzed asymmetric arylation. The aza-Achmatowicz rearrangement and hydrogenation steps further convert the intermediate into the desired piperidone. The synthetic utility of this piperidone is demonstrated by synthesizing a NK1 receptor antagonist. This method is advantageous due to its short synthetic route, high yield, minimal loss of optical purity, and the use of a renewable biomass-derived starting material, addressing sustainability and environmental concerns associated with traditional methods and the disposal of agricultural waste.