3-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one

Base Information

• Chemical Name: 3-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one
• CAS No.: 167933-07-5
• Molecular Formula: C₂₀H₂₁F₃N₄O
• Molecular Weight: 390.408
• DSSTox Substance ID: DTXSID30168445
• Mol file: 167933-07-5.mol

Synonyms:3-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one;SCHEMBL678268;BDBM84952;DTXSID30168445;CCIZQGRSEAHATK-UHFFFAOYSA-N;PDSP1_001329;PDSP2_001313;AKOS015899995;AC-1628;BCP9000690;CAS_127941;NSC_127941;SB18524;AS-35137

Chemical Property of 3-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one

Chemical Property:

• Appearance/Colour: white powder
• Refractive Index: 1.566
• PKA: 12.12±0.30(Predicted)
• PSA: 44.27000
• Density: 1.292 g/cm³
• LogP: 3.17350
• Storage Temp.: 2-8°C
• Solubility.: DMSO: soluble10mg/mL, clear
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 390.16674579
• Heavy Atom Count: 28
• Complexity: 542

Purity/Quality:

99.8% ^*data from raw suppliers

Flibanserin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CN(CCN1CCN2C3=CC=CC=C3NC2=O)C4=CC=C(C=C4)C(F)(F)F
• description: Flibanserin (Addyi-Sprout Pharmaceuticals) is a first-in-class oral medication approved by FDA for the treatment of acquired, generalized hypoactive sexual desire disorder (HSDD) in premenopausal women. Although it meets the need for drugs that address women's sexual function, flibanserin is unlike agents that treat erectile dysfunction, as it is intended to increase sexual desire, not performance. Flibanserin is the first prescription medicine for the treatment of this sexual dysfunction. The FDA approval is not without warnings; flibanserin is subject to the Risk Evaluation and Mitigation Strategy (REMS) to ensure safe use by patients, and has a boxed warning directed to prescribing providers. The goal is to inform patients and providers of the increased risk of hypotension and syncope (Vallejos 2017).
• Uses: Filbanserin is an agonist of serotonin-5HT1A receptor and an antagonist of the 5-HT2A receptor. Binds dopamine receptors with Ki values ranging from 4-24 nM. Used to treat hypoactive sexual desire disorder in females. Antidepressant (5-HT1a agonist and 5-HT2 antagonist).
• Description: Flibanserin is a drug originally developed by Boehringer-Ingelheim and later Sprout Pharmaceuticals, which was approved in 2015 by the FDA for the treatment of premenopausal women with hypoactive sexual desire disorder (HSDD). The drug, which was originally developed for the treatment of depression by Boehringer- Ingelheim, is a full agonist of the 5-HT1A receptor, an antagonist of the 5-HT2A receptor, and a partial agonist of the dopamine-4 (D4) receptor, which triggers increased dopamine and norepinephrine levels along with decreased serotonin levels. In three randomized trials involving 2400 premenopausal women, the drug was found to increase the number of satisfying sexual events by 0.5-1.0 events per month and increased sexual desire on average by 10-12% over placebo. Side effects include decreased blood pressure and loss of consciousness, especially in subjects who consumed alcohol.

Technology Process of 3-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-one

There total 27 articles about 3-[2-[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]ethyl]-1H-benzimidazol-2-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: 92.5%

BIMT 17 hydrochloride (147359-76-0) → flibanserin (167933-07-5)

Guidance literature:

With potassium carbonate; In ethanol; water; at 80 ℃; for 2h; Solvent; Temperature; Reagent/catalyst; Autoclave; Large scale;

Reference yield: 92.3%

1-(prop-1-en-2-yl)-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethyl)-1H-benzo[d]imidazol-2(3H)-one (1971858-36-2) → flibanserin (167933-07-5)

Guidance literature:

With hydrogenchloride; In ethanol; water; at 0 - 35 ℃; Solvent; Temperature;

Reference yield: 90.0%

1,3-dihydro-1-[2-(1-piperazinyl)ethyl]-2H-benzimidazol-2-one + 3-bromo-1-trifluoromethylbenzene (401-78-5) → flibanserin (167933-07-5)

Guidance literature:

With [2,2]bipyridinyl; nickel diacetate; sodium hydride; In sulfolane; at 100 ℃; for 10h; Solvent;

upstream raw materials:

3-bromo-1-trifluoromethylbenzene

1-(prop-1-en-2-yl)-3-(2-(4-(3-(trifluoromethyl)phenyl)piperazin-1-yl)ethyl)-1H-benzo[d]imidazol-2(3H)-one

1,2-diamino-benzene

1,3-dihydro-1-(1-methylethenyl)-2H-benzimidazol-2-one

Refernces

• 1、 -. "A new method for synthesizing flibanserin (by machine translation)". . . Retrieved 2019/02/04.
• 2、 -. "Preparation method of flibaserin". Paragraph 0025; 0031; 0038. . Retrieved 2018/09/14.