180272-14-4

Basic information

• Product Name: SOLIFENACIN
• Synonyms: 1(S)-Phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid 3(R)-quinuclidinyl ester;Solifenacin;quinuclidin-3-yl 1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate;(R)-quinuclidin-3-yl (S)-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate
• CAS NO: 180272-14-4
• Molecular Formula: C23H26N2O2
• Molecular Weight: 362.47
• Mol File: 180272-14-4.mol
• Article Data: 43

Chemical Properties

• Boiling Point: 505.5 °C at 760 mmHg
• Flash Point: 259.5 °C
• Appearance: /
• Density: 1.24 g/cm³
• Vapor Pressure: 2.41E-10mmHg at 25°C
• Refractive Index: 1.648
• PKA: 9.03±0.33(Predicted)
• CAS DataBase Reference: SOLIFENACIN(CAS DataBase Reference)
• NIST Chemistry Reference: SOLIFENACIN(180272-14-4)
• EPA Substance Registry System: SOLIFENACIN(180272-14-4)

Safety Data

• Hazardous Substances Data: 180272-14-4(Hazardous Substances Data)

Usage

Description

SOLIFENACIN, also known as Racemic Solifenacin Succinate, is a muscarinic M3 receptor antagonist derived from hydrolyzable tannins found in various plant sources. It possesses properties that enable it to interact with biopolymers and macromolecules, making it a promising pharmaceutical candidate for specific applications.
Used in Pharmaceutical Industry:
SOLIFENACIN is used as a muscarinic M3 receptor antagonist for the treatment of urinary incontinence. It works by blocking the action of acetylcholine on the M3 receptors, which helps to reduce overactive bladder contractions and improve bladder control.

InChI:InChI=1/C23H26N2O2/c26-23(27-21-16-24-13-10-18(21)11-14-24)25-15-12-17-6-4-5-9-20(17)22(25)19-7-2-1-3-8-19/h1-9,18,21-22H,10-16H2/t21-,22-/m0/s1

Upstream product

• 52250-50-7 1-phenyl-3,4-dihydroisoquinoline 
• 1251905-45-9 methyl (1S)-1-phenyl-3,4-dihydro-2(1H)-isoquinoline-carboxylate 
• 124-41-4 sodium methylate 
• 25333-42-0 (R)-quinuclidin-3-ol 
• 20194-18-7 sodium phenyl-methanolate 
• 22990-19-8 (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1203447-95-3 phenyl (S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate 
• 141-52-6 sodium ethanolate 
• 541-41-3 chloroformic acid ethyl ester 
• 627-11-2 2-Chloroethyl chloroformate 
• 180272-45-1 (R)-(-)-1-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 881834-78-2 4-nitrophenyl-1-phenyl-3,4-dihydroisoquinoline-2(1H)-carboxylate 
• 22990-19-8 1-phenyl-1,2,3,4-tetrahydroisoquinoline 

Downstream Products

• 180468-37-5 Solifenacin hydrochloride 
• 1354548-49-4 1-azabicyclo[2.2.2]oct-8-yl (1S)-1-phenyl-3,4-dihydro-1H-isoquinoline-2-carboxylate fumarate 
• 180272-28-0 (1'S,3R)-3-[[(1'-phenyl-1',2',3',4'-tetrahydro-2'-isoquinolyl)carbonyl]oxy]quinuclidine 1-oxide 
• 1172614-17-3 solifenacin hydrogen adipate 
• 865813-75-8 (-)-(3R)-quinuclidin-3-yl (1R)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate naphthalene-2-sulfonate 

Relevant articles and documents

Synthesis process of solifenacin succinate

The invention discloses a synthesis process of solifenacin succinate, and relates to the technical field of medicines. The preparation method comprises the following steps: step 1, reacting (R)-quinuclidin-3-ol (B) with a reaction substance to generate (R)-quinuclidin-3-yl carbonochloridate (C); step 2, enabling (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline (A) to react with (R)-quinuclidin-3-yl carbonochloridate (C) to generate solifenacin (D); and step 3, using the solifenacin (D) to prepare the solifenacin succinate. After the technical scheme is adopted, the method has the beneficial effects that in the synthesis process, the problem of low conversion rate caused by direct ester exchange reaction is avoided, meanwhile, the probability of reversible reaction caused by nucleophilic intermediate products generated in the condensation process is also reduced, and the reaction is greatly promoted, so that the yield of solifenacin succinate is increased, the reaction conditions are mild, the operation is simple, the operation procedures are reduced, and the method is suitable for large-scale production.

Solifenacin succinate new preparation method

The present invention relates to a solifenacin succinate new preparation method which mainly comprises the following steps: 1) formula III compound (R)-(-)-quinuclidin-3-ol and formula IV compound N,N,-N,N-carbonyldiimidazole are reacted to obtain formula V compound (R)-imidazole-1-carboxylic acid-1-azabicyclo[2,2,2] octyl ester; 2) the formula V compound (R)-imidazole-1-carboxylic acid-1-azabicyclo[2,2,2] octyl ester is reacted with formula VI compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline to obtain a formula II solifenacin alkaline body; 3) the formula II solifenacin alkaline body isreacted with succinic acid, refined and purified to obtain formula I solifenacin succinate. The preparation method has the advantages that the yield of the solifenacin succinate is high and the purityis high, and the process is simple and suitable for industrial production.

A process for the preparation of new thorley that succinic acid

The invention relates to a method for preparing a solifenacin succinate ((3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate succinate). The method comprises the following steps: 1) preparing a compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline carboxylic acid ethyl ester of formula III from a compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline, serving as a raw material, of formula IV; 2) synthesizing a compound (3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate of formula II in an ionic liquid by using the compound (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline carboxylic acid ethyl ester of formula III; and 3) salifying the compound (3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate of formula II in an organic solvent to obtain the compound solifenacin succinate ((3R)-1-azabicyclo [2.2.2] octane-3-yl (1S)-1-phenyl-3,4-dihydroisoquinoline-2-(1H)-carboxylate succinate) of formula I. The preparation method has the advantages that the process is simple, the method is suitable for industrialized production, the yield of the product is high and the purity of the product is high.