100615-14-3

Basic information

• Product Name: 1-Cyclohexyl-3H-1,3-benzodiazol-2-one
• Synonyms: 1-Cyclohexyl-3H-1,3-benzodiazol-2-one
• CAS NO: 100615-14-3
• Molecular Formula: C₁₃H₁₆N₂O
• Molecular Weight: 216.27894
• Mol File: 100615-14-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1-Cyclohexyl-3H-1,3-benzodiazol-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Cyclohexyl-3H-1,3-benzodiazol-2-one(100615-14-3)
• EPA Substance Registry System: 1-Cyclohexyl-3H-1,3-benzodiazol-2-one(100615-14-3)

Safety Data

• Hazardous Substances Data: 100615-14-3(Hazardous Substances Data)

Usage

Class

Benzodiazole organic compounds

Function

Selective agonist for the κ-opioid receptor

Potential uses

Treatment of addiction, pain management, and anxiety disorders

Research interest

Unique pharmacological profile and potential therapeutic applications

Additional research

Needed to fully understand its effects and potential medical uses

Upstream product

• 74628-31-2 N-1-cyclohexylbenzene-1,2-diamine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 3190-03-2 1,3-dihydrospiro[2H-benzimidazole-2,1'-cyclohexane] 

Downstream Products

• 929565-30-0 1-cyclohexyl-3-[(1R)-3-(chloro)-1-phenylpropyl]-1,3-dihydro-2H-benzimidazol-2-one 

Relevant articles and documents

Synthesis and activity of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors

A series of novel 1- or 3-(3-amino-1-phenyl propyl)-1,3-dihydro-2H-benzimidazol-2-ones as selective norepinephrine reuptake inhibitors was discovered. Several compounds such as 15 and 20 showed good hNET potency. Compounds 15 and 20 also displayed excellent selectivity at hNET that appeared superior to those of reboxetine and atomoxetine (4 and 5).

Rearrangement of spiro-benzimidazolines: preparation of N-alkenyl- and N-alkyl-benzimidazol-2-ones

A synthetically useful protocol has been developed for the preparation of highly functionalized N-alkenyl-benzimidazol-2-ones. Reaction of commercially available o-phenylenediamines with variously substituted cyclic ketones provides spiro-benzimidazolines. Treatment of these spiro-benzimidazolines with triphosgene in the presence of potassium carbonate results in rapid rearrangement and formation of N-alkenyl-benzimidazol-2-ones in modest to excellent yield for the two-step sequence. Extension of this methodology toward the preparation of a μ opiate receptor antagonist and droperidol, a potent antiemetic and antipsychotic agent, currently a marketed pharmaceutical is also described. Upon treatment of spiro-benzimidazolines with triphosgene in the presence of sodium triacetoxyborohydride, N-alkyl-benzimidazol-2-ones were formed.

Substituted propylamine derivatives and methods of their use

The present invention is directed to substituted propylamine derivatives of formula I: or a pharmaceutically acceptable salt thereof, compositions containing these derivatives, and methods of their use for the prevention and treatment of conditions ameliorated by monoamine reuptake including, inter alia, vasomotor symptoms (VMS), sexual dysfunction, gastrointestinal and genitourinary disorders, chronic fatigue syndrome, fibromylagia syndrome, nervous system disorders, and combinations thereof, particularly those conditions selected from the group consisting of major depressive disorder, vasomotor symptoms, stress and urge urinary incontinence, fibromyalgia, pain, diabetic neuropathy, and combinations thereof.