133099-11-3

Basic information

• Product Name: (S)-alpha,alpha-Diphenyl-3-pyrrolidineacetamide
• Synonyms: (s)-alpha,alpha-diphenyl-3-pyrrolidineacetamide;(S)-(+)-Alfa,Alfa-Diphenyl-3-Pyrrolidine acetamide;(S)-2,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide;(S)-ALPHA,ALPHAL-DIPHENYL-3-PYRROLIDINEACETAMIDE,96%;(S)-α,α-Diphenyl-3-pyrrolidineacetamide;(3S)-α,α-Diphenyl-3-pyrrolidineacetonitrile;diphenyl[(S)-pyrrolidin-3-yl]acetonitrile
• CAS NO: 133099-11-3
• Molecular Formula: C₁₈H₁₈N₂
• Molecular Weight: 280.36
• Product Categories: Pharmaceutical material and intermeidates
• Mol File: 133099-11-3.mol

Chemical Properties

• Boiling Point: 488.5°C at 760 mmHg
• Flash Point: 249.2°C
• Appearance: /
• Density: 1.147g/cm³
• Vapor Pressure: 1.08E-09mmHg at 25°C
• Refractive Index: 1.596
• PKA: 9.46±0.10(Predicted)
• CAS DataBase Reference: (S)-alpha,alpha-Diphenyl-3-pyrrolidineacetamide(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-alpha,alpha-Diphenyl-3-pyrrolidineacetamide(133099-11-3)
• EPA Substance Registry System: (S)-alpha,alpha-Diphenyl-3-pyrrolidineacetamide(133099-11-3)

Safety Data

• Hazardous Substances Data: 133099-11-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(S)-alpha,alpha-Diphenyl-3-pyrrolidineacetamide is used as a degradation product and impurity compound for darifenacin, a medication used to treat overactive bladder. Its presence is important for quality control and ensuring the safety and efficacy of the drug.

InChI:InChI=1/C18H20N2O/c19-17(21)18(16-11-12-20-13-16,14-7-3-1-4-8-14)15-9-5-2-6-10-15/h1-10,16,20H,11-13H2,(H2,19,21)/t16-/m1/s1

Upstream product

• 371240-55-0 (S)-3-(toluene-4-sulfonyloxy)pyrrolidin-1-ylcarboxylic acid tert-butyl ester 
• 86-29-3 Diphenylacetonitrile 
• 1189753-52-3 (S)-2,2-diphenyl-2-[1-(tert-butyloxycarbonyl)-3-pyrrolidinyl]acetonitrile 
• 197964-14-0 2,2-diphenyl-2-[(3S)-N-benzyl-pyrrolidin-3-yl]acetonitrile 
• 851645-39-1 (S)-1-benzyl-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine hydrochloride 
• 133099-09-9 (S)-diphenyl-[1-(toluene-4-sulfonyl)-pyrrolidin-3-yl]-acetonitrile 

Downstream Products

• 134002-26-9 (S)-2,2-diphenyl-2-(pyrrolidin-3-yl)-acetamide L-tartrate 
• 586346-94-3 darifenacin hydrochloride 
• 133099-04-4 darifenacin 
• 133099-07-7 (S)-darifenacin hydrobromide 
• 103887-32-7 3-(R,S)-(1-carbamoyl-1,1-diphenyl-methyl)pyrrolidine 
• 134002-25-8 2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide 

Relevant articles and documents

Synthesis of Arylethylamines via C(sp3)-C(sp3) Palladium-Catalyzed Cross-Coupling

Substituted arylethylamines represent a key structural motif in natural, pharmaceutical, and agrochemical compounds. Access to such scaffolds has been the subject of long-standing synthetic interest. Herein, we report the synthesis of such scaffolds via a palladium-catalyzed C(sp3)-C(sp3) coupling between (chloromethyl)aryls and air-/moisture-stable N,N-dialkylaminomethyltrifluoroborate salts. Rapid hit identification was achieved using microscale high-throughput experimentation and was followed by millimolar-scale reaction parameter optimization. A range of structurally and electronically varied arylethylamine products were obtained in moderate to excellent yields (27-96%, >60 examples). The reaction mechanism is proposed to proceed via formation of a trialkylbenzylammonium species prior to oxidative addition.

A new solvent system (Cyclopentyl methyl ether-water) in process development of darifenacin HBr

Darifenacin is a potent and competitive M3 selective receptor antagonist (M3SRA), and its hydrobromide salt (1) is the active ingredient of pharmaceutical formulations for oral treatment of urinary incontinence. The present work demonstrates an efficient, commercial manufacturing process for darifenacin hydrobromide (1).

PROCESS FOR PREPARATION OF DARIFENACIN AND INTERMEDIATES USED IN THE PROCESS

Disclosed herein is a process for the preparation of darifenacin and physiologically acceptable salts thereof. Also disclosed is a compound of formula X: wherein R is linear or branched C 1-10 alkyl, phenyl, tolyl, ortho-, meta- or para- xylyl

METHOD OF PRODUCING (S)-3-(1-CYANO-1,1-DIPHENYLMETHYL)-PYRROLIDINE

The present application relates to a method of (S)-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine by reacting an (S)-1-protected-3-(sulfonyloxy)-pyrrolidine having an easily deprotectable protecting group with diphenylacetonitrile in the presence of a base to obtain an (S)-1-protected-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine and then deprotecting the obtained compound under a mild condition. According to the method of the present invention, it is possible to efficiently produce (S)-3-(1-cyano-1,1-diphenylmethyl)-pyrrolidine, which is an important intermediate in the process of producing a muscarinic receptor antagonist such as darifenacin.

PROCESS FOR PREPARING 3-SUBSTITUTED PYRROLIDINE COMPOUNDS

Disclosed is a process for preparing 3 -substituted pyrrolidine compounds of formula (VII) or salts thereof, wherein R1 is described herein, which are intermediate compounds useful for the synthesis of darifenacin which is indicated for the treatment of overactive bladder with symptoms of urge, urinary incontinence, and the like, and pharmaceutically acceptable salts thereof. Also disclosed is a process for preparing darifenacin and pharmaceutically acceptable salts thereof.

SUBSTITUTED PYRROLIDINES

Disclosed herein are substituted pyrrolidine-based muscarinic receptor modulators of Formula I, process of preparation thereof, pharmaceutical compositions thereof, and methods of use thereof.

NOVEL AND IMPROVED PROCESSES FOR THE PREPARATION OF INTERMEDIATES OF DARIFENACIN, DARIFENACIN AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention relates to novel and improved processes for the preparation of intermediates of darifenacin, darifenacin and its pharmaceutically acceptable salts. Darifenacin is chemically known as 3 -(S)-(-)-(l -carbamoyl- 1,1 -diphenylmethyl)-l- [2- (2,3-dihydro benzofuran-5-yl)ethyl]pyrrolidine and represented by formula-2. The invention also relates to the novel polymorphs of the pharmaceutically acceptable salts of darifenacin and the methods for their re aration.

Quaternary ammonium diphenylmethyl compounds useful as muscarinic receptor antagonists

The invention provides compounds of formula I: in salt or zwitterionic form or a pharmaceutically acceptable salt thereof, wherein R1-6, a-e and Q are as defined in the specification. These compounds are muscarinic receptor antagonists. The inv

PREPARATION OF DARIFENACIN AND ITS SALTS

Provided are various processes and compounds related to darifenacin and/or its salts. For example, there is provided a process for preparing a free base of darifenacin: Formula, or the salt thereof, the process including reacting 3-(S)-(cyanodiphenylmethyl)-1-[2-(2,3-dihydrobenzofuran-5-yl) ethyl] pyrrolidine of the Formula (IV), or a salt thereof: Formula (IV) with a base effective to convert the nitrile group of the compound of the Formula (IV) to the amide group of the darifenacin in an organic solvent, the reaction being carried out in the organic solvent, with a proviso that the solvent is not 2-methyl-butan-2-ol, and with further proviso that the reaction produces less than about 0.5 % of the compound of the Formula (Ic): Formula (Ic) in the reaction mass, as measured by HPLC. Various embodiments and variants are provided.

SUBSTITUTED 4-AMINO-1-BENZYLPIPERIDINE COMPOUNDS

This invention provides 4-amino-1-benzylpiperidine and related compounds and pharmaceutically acceptable salts thereof which are useful as muscarinic receptor antagonists. This invention also provides pharmaceutical compositions containing such compounds; processes and intermediates useful for preparing such compounds; and methods for treating disease conditions mediated by muscarinic receptors, such as overactive bladder, irritable bowel syndrome, asthma and chronic obstructive pulmonary disease, using such compounds.