Solifenacin

Base Information

• Chemical Name: Solifenacin
• CAS No.: 242478-37-1
• Molecular Formula: C23H26N2O2
• Molecular Weight: 362.472
• UNII: A8910SQJ1U
• DSSTox Substance ID: DTXSID3048289
• Nikkaji Number: J1.594.869H
• Wikipedia: Solifenacin
• Wikidata: Q59575279
• NCI Thesaurus Code: C75284
• RXCUI: 322167
• Pharos Ligand ID: Q1WMDTJ5M4KW
• Metabolomics Workbench ID: 43581
• ChEMBL ID: CHEMBL1734
• Mol file: 242478-37-1.mol

Synonyms:2(1H)-Isoquinolinecarboxylic acid, 3,4-dihydro-1-phenyl-,1- azabicyclo(2.2.2)oct-3-yl ester, (R-(R*,S*))-;905, YM;quinuclidin-3'-yl-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate monosuccinate;solifenacin;solifenacin succinate;Succinate, Solifenacin;vesicare;YM 905;YM905

Chemical Property of Solifenacin

Chemical Property:

• Vapor Pressure: 2.41E-10mmHg at 25°C
• Refractive Index: 1.648
• Boiling Point: 505.5 °C at 760 mmHg
• PKA: 9.03±0.33(Predicted)
• Flash Point: 259.5 °C
• PSA: 32.78000
• Density: 1.24 g/cm³
• LogP: 3.74070
• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 362.199428076
• Heavy Atom Count: 27
• Complexity: 525

Purity/Quality:

98%min ^*data from raw suppliers

Solifenacin 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticholinergic Agents
• Canonical SMILES: C1CN2CCC1C(C2)OC(=O)N3CCC4=CC=CC=C4C3C5=CC=CC=C5
• Isomeric SMILES: C1CN2CCC1[C@H](C2)OC(=O)N3CCC4=CC=CC=C4[C@@H]3C5=CC=CC=C5
• Recent ClinicalTrials: Efficacy and Safety of High Dose Vitamin D Supplementation for Overactive Bladder Dry in Children
• Recent EU Clinical Trials: PERIPHERAL TRANSCUTANEOUS NEUROMODULATION OF THE POST-TIBIAL NERVE (T-PTNS) FOR SOLIFENACIN 10mg. IN THE TREATMENT OF HYPERACTIVE BLADDER SYNDROME: NON-INFERIORITY PHASE IV RANDOMIZED CLINICAL TRIAL
• Recent NIPH Clinical Trials: Study on the safety and efficacy of anticolinergics for children with overactive bladder
• Uses: muscarinic M3 antagonist

Technology Process of Solifenacin

There total 65 articles about Solifenacin 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: 96.8%

C34H29NO2P(1+)*Cl(1-) + (R)-quinuclidin-3-ol (25333-42-0) → solifenacin (242478-37-1,180272-14-4)

Guidance literature:

In toluene; at 60 - 70 ℃; Temperature;

Reference yield: 95.1%

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline (180468-42-2) + (R)-quinuclidin-3-ol (25333-42-0) → solifenacin (242478-37-1,180272-14-4)

Guidance literature:

With sodium hydride; 1-butyl-3-methylimidazolium Tetrafluoroborate; In N,N-dimethyl-formamide; at 100 ℃; for 6h; Temperature; Concentration;

Reference yield: 92.2%

(3S)-1-azabicyclo[2.2.2]octan-3-yl 1H-imidazole-1-carboxylate + (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (22990-19-8,96719-89-0,118864-75-8) → solifenacin (242478-37-1,180272-14-4)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 2h; Inert atmosphere;

upstream raw materials:

(S)-N-carboxylic acid ethyl ester-1-phenyl-1,2,3,4-tetrahydroisoquinoline

(R)-quinuclidin-3-ol

1-phenyl-3,4-dihydroisoquinoline

N-phenethylbenzamide

Downstream raw materials:

Solifenacin hydrochloride

solifenacin succinate

(1S)-3,4-dihydro-1-phenyl-2-(1H)-isoquinolinecarboxylic acid (3S)-1-azabicyclo[2.2.2]oct-3-yl ester succinate

(3R)-1-azabicyclo[2.2.2]oct-3-yl (1R)-3,4-dihydro-1-phenyl-2(1H)-isoquinoline carboxylate succinate

Refernces

• 1、 -. "Asymmetric synthesis method for preparation of solifenacin". Paragraph 0172; 0173; 0174. . Retrieved 2018/07/10.
• 2、 -. "A succinic acid thorley that new preparation method". . . Retrieved 2017/09/19.