111982-45-7

Usage

Uses

Used in Pharmaceutical Industry:
2-Fluorophenyl cyclopentyl ketone is used as an intermediate for the synthesis of various pharmaceutical compounds, contributing to the development of new drugs and medications.
Used in Organic Compounds Production:
FPCPK serves as a building block in the production of organic compounds, including agrochemicals and other specialty chemicals, playing a crucial role in the synthesis of these compounds for various applications.
Safety Precautions:
2-Fluorophenyl cyclopentyl ketone is considered potentially hazardous if inhaled, ingested, or comes into contact with the skin or eyes. Proper safety measures should be in place to handle 2-FLUOROPHENYL CYCLOPENTYL KETONE safely and minimize the risk of exposure.

InChI:InChI=1/C12H13FO/c13-11-8-4-3-7-10(11)12(14)9-5-1-2-6-9/h3-4,7-9H,1-2,5-6H2

Synthetic route

Cyclopentyl bromide (137-43-9) + 2-fluorobenzonitrile (394-47-8) → cyclopentyl-(2-fluorophenyl)ketone (111982-45-7)

Conditions	Yield
Stage #1: Cyclopentyl bromide With iodine; magnesium In tetrahydrofuran at 20℃; Reflux; Stage #2: 2-fluorobenzonitrile With copper(I) bromide dimethylsulfide complex In tetrahydrofuran for 4h; Inert atmosphere; Reflux; Stage #3: With sulfuric acid; water In tetrahydrofuran for 4h; Reagent/catalyst; Solvent; Time;	90%

2-fluorobenzonitrile (394-47-8) + cyclopentylmagnesium bromide (33240-34-5) → cyclopentyl-(2-fluorophenyl)ketone (111982-45-7)

Conditions	Yield
Stage #1: 2-fluorobenzonitrile; cyclopentylmagnesium bromide With copper(I) bromide In tetrahydrofuran at 60℃; for 15h; Stage #2: With sulfuric acid; water In tetrahydrofuran at 0℃; for 15h;	40%

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → α-bromocyclopentyl-(2-fluorophenyl)ketone (1616657-67-0)

Conditions	Yield
Stage #1: cyclopentyl-(2-fluorophenyl)ketone With hydrogen bromide In water at 20℃; for 0.0833333h; Darkness; Stage #2: With lithium chloride In water at 20℃; for 0.0166667h; Darkness; Stage #3: With dihydrogen peroxide In water at 70℃; for 1.5h; Darkness;	96%

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → 3-cyclopentyl-1H-indazole (859164-86-6)

Conditions	Yield
With hydrazine In water at 130℃; for 72h;	89%

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → C14H16OS (1372151-92-2)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 18 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 5 °C View Scheme

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → C14H15BrS

Conditions	Yield
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 18 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 5 °C 3.1: phosphorus tribromide / diethyl ether / 1 h / 20 °C View Scheme

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → C18H25O3PS

Conditions	Yield
Multi-step reaction with 4 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 18 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 5 °C 3.1: phosphorus tribromide / diethyl ether / 1 h / 20 °C 4.1: toluene / 18 h / Reflux View Scheme

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → C25H29F2O3PS

Conditions	Yield
Multi-step reaction with 5 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C 1.2: 18 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / 0 - 5 °C 3.1: phosphorus tribromide / diethyl ether / 1 h / 20 °C 4.1: toluene / 18 h / Reflux 5.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -70 °C 5.2: 0.5 h / -70 - 20 °C View Scheme

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) + ethyl 2-sulfanylacetate (623-51-8) → C16H18O2S (1372151-88-6)

Conditions	Yield
Stage #1: ethyl 2-sulfanylacetate With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: cyclopentyl-(2-fluorophenyl)ketone In N,N-dimethyl-formamide for 18h; Reflux;

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → α-hydroxycyclopentyl-(2-flourophenyl)-N-methylamine (111982-48-0) + (2-fluorophenyl)(1-hydroxycyclopentyl)methanone (1616657-68-1)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: hydrogen bromide / water / 0.08 h / 20 °C / Darkness 1.2: 0.02 h / 20 °C / Darkness 1.3: 1.5 h / 70 °C / Darkness 2.1: 6 h / -40 °C View Scheme

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → (±)-2-(2-fluorophenyl)-2-(methylamino)cyclohexanone (111982-50-4)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: hydrogen bromide / water / 0.08 h / 20 °C / Darkness 1.2: 0.02 h / 20 °C / Darkness 1.3: 1.5 h / 70 °C / Darkness 2.1: 6 h / -40 °C 3.1: palladium dichloride / decalin / 4 h / Reflux View Scheme

cyclopentyl-(2-fluorophenyl)ketone (111982-45-7) → 1-(2-fluorophenyl)-N-methyl-2-oxocyclohexanaminium chloride (111982-49-1)

Conditions	Yield
Multi-step reaction with 4 steps 1.1: hydrogen bromide / water / 0.08 h / 20 °C / Darkness 1.2: 0.02 h / 20 °C / Darkness 1.3: 1.5 h / 70 °C / Darkness 2.1: 6 h / -40 °C 3.1: palladium dichloride / decalin / 4 h / Reflux 4.1: hydrogenchloride / water; dichloromethane View Scheme

Upstream product

• 137-43-9 Cyclopentyl bromide 
• 394-47-8 2-fluorobenzonitrile 
• 33240-34-5 cyclopentylmagnesium bromide 

Downstream Products

• 1616657-67-0 α-bromocyclopentyl-(2-fluorophenyl)ketone 
• 111982-48-0 α-hydroxycyclopentyl-(2-flourophenyl)-N-methylamine 
• 1616657-68-1 (2-fluorophenyl)(1-hydroxycyclopentyl)methanone 
• 111982-50-4 (±)-2-(2-fluorophenyl)-2-(methylamino)cyclohexanone 
• 111982-49-1 1-(2-fluorophenyl)-N-methyl-2-oxocyclohexanaminium chloride 

Relevant academic research and scientific papers

ARYLCYCLOHEXYLAMINE DERIVATIVES AND THEIR USE IN THE TREATMENT OF PSYCHIATRIC DISORDERS

Provided herein are arylcyclohexylamine derivatives and their use in the treatment of psychiatric disorders.

Synthesis of 2-(2-fluorophenyl)-2-methylamino-cyclohexanone as a new ketamine derivative

The main goal of this article is to the present research on the development of ketamine derivatives. The target molecule was a fluoroderivative of ketamine, for which a multistep synthesis has been reported. This novel ketamine derivative, 2-(2-fluorophenyl)-2-methylamino-cyclohexanone, has been called fluoroketamine by our research group. The starting fluorobenzonitrile was reacted with the appropriate Grignard reagent followed by the bromination reaction to obtain α-bromocyclopentyl-(2-fluorophenyl)-ketone. The reaction of the obtained ketone with methylamine at -40 °C then resulted in the formation of α-hydroxycyclopentyl-(2-flourophenyl)-N-methylamine. Finally, the five-memberd ring cyclopentanol was expanded to the cyclohexylketone by a thermal rearrangement reaction. The HCl salt of the target molecule, which is soluble in water, was obtained by the acidification of the free fluoroketamine with HCl. Preliminary animal tests on mice have shown that the resulting fluoroketamine has some advantages over ketamine in terms of the effective dose and the recovery time. Copyright

CB1 MODULATOR COMPOUNDS

Novel compounds of structural formula (I) are disclosed. As modulators of the Cannabinoid-1 (CB1) receptor, these compounds are useful in the treatment, prevention and suppression of diseases mediated by the CB1 receptor. As such, compounds of the present invention are useful as in the treatment, prevention and suppression of psychosis, memory deficits, cognitive disorders, migraine, neuropathy, neuro-inflammatory disorders (e.g., multiple sclerosis, Guillain-Barre syndrome and the inflammatory sequelae of viral encephalitis), cerebral vascular accidents, head trauma, anxiety disorders, stress, epilepsy, Parkinson's disease, and schizophrenia. The compounds are also useful for the treatment of substance abuse disorders, particularly to opiates, alcohol, and nicotine. The compounds are also useful for the treatment of obesity or eating disorders associated with excessive food intake and complications associated therewith.