124936-74-9

Basic information

• Product Name: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol
• Synonyms: 2-[3-[BIS(1-METHYLETHYL)AMINO]-1-PHENYLPROPYL]-4-METHYLPHENOL MONOHYDROBROMIDE;(R)-2,3-BIS(1-METHYLETHYL)AMINO-1-PHENYLPROPYL-4-METHYLPHENOL;TOLTERODINE HYDROBROMIC ACID SALT;2-[3-BIS(1-METHYLETHYL)AMINO]-1-PHENYLPROPYL]-4-METHYLPHENOL HBR;2-[3-[BIS(1-METHYLETHYL)AMINO]-1-PHENYLPROPY]-4-METHYLPHENYL MONOHYDROBROMIDE;N,N-Diisopropyl-3-(2-Hydroxy-5-Methylphenyl)-3-PhenylPropylAmine(ForTolterodine-L-Tartrate);2-(3-(Bis(1-methylethyl)amino)-1-phenylpropyl)-4-methylphenylmonohydrobromide;2-[3-[bis(1-methylethyl)amino]1-phenylpropyl]-4-methyl phenol monohydrobromide (intermediate of tolterodine tartrate)
• CAS NO: 124936-74-9
• Molecular Formula: C₂₂H₃₁NO
• Molecular Weight: 325.49
• Product Categories: (intermediate of tolterodine tartrate)
• Mol File: 124936-74-9.mol

Chemical Properties

• Melting Point: 72.3-73.5 °C
• Boiling Point: 473°C at 760 mmHg
• Flash Point: 239.9°C
• Appearance: /
• Density: 1.003±0.06 g/cm3(Predicted)
• Vapor Pressure: 1.44E-09mmHg at 25°C
• PKA: 10.13±0.48(Predicted)
• CAS DataBase Reference: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol(124936-74-9)
• EPA Substance Registry System: 2-[3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-methylphenol(124936-74-9)

Safety Data

• Hazardous Substances Data: 124936-74-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Iprindole is used as an antidepressant medication for the treatment of depression. It is particularly effective in enhancing mood and reducing the symptoms associated with depressive disorders.
Used in Neurology:
In the field of neurology, Iprindole serves as a mood stabilizer, helping to regulate the levels of serotonin and norepinephrine in the brain, which are essential for maintaining emotional balance and preventing mood swings.
Used in Research:
Iprindole is also utilized in scientific research to study the mechanisms of action of tricyclic antidepressants and their impact on neurotransmitter reuptake, providing valuable insights into the development of new treatments for mood disorders.

InChI:InChI=1/C22H31NO.BrH/c1-16(2)23(17(3)4)14-13-20(19-9-7-6-8-10-19)21-15-18(5)11-12-22(21)24;/h6-12,15-17,20,24H,13-14H2,1-5H3;1H

Upstream product

• 108-18-9 diisopropylamine 
• 209747-04-6 2-hydroxy-6-methyl-4-phenyldihydrobenzopyran 
• 106-44-5 p-cresol 
• 906532-26-1 3-(N,N-diisopropylamino)-1-phenylpropan-1-ol 
• 124935-88-2 N,N-diisopropyl-3-(2-methoxy-5-methylphenyl)-3-phenylpropan-1-amine 
• 906532-18-1 diisopropyl-(3-phenyl-3-p-toluyloxypropyl)amine 
• 897314-72-6 (+/-)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propanamide 
• 837376-36-0 3-(2-hydroxy-5-methylphenyl)-N,N-diisopropyl-3-phenylpropan-1-aminium bromide 
• 944241-58-1 racemic tolterodine hydrogen sulfate 
• 173948-30-6 (E)-N,N-diisopropyl-3-phenylprop-2-en-1-amine 
• 1055330-27-2 3-hydroxy-3-phenylpropyl 4-nitrobenzene sulfonate 
• 4850-49-1 1-phenyl-1,3-propanediol 
• 14371-10-9 (E)-3-phenylpropenal 
• 959624-24-9 (2-hydroxy-4-phenyl-3,4-dihydro-2H-chromen-6-yl)methanol 

Downstream Products

• 873551-03-2 (S)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate 
• 209747-05-7 (+)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropylamine L-hydrogen tartrate 
• 124937-52-6 tolterodine tartrate 
• 944241-58-1 racemic tolterodine hydrogen sulfate 
• 1043911-42-7 N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenyl-propylamine L-tartrate 
• 948844-07-3 (R)-N,N-diisopropyl-3-(2-hydroxy-5-methylphenyl)-3-phenylpropanamine L-hydrogen tartrate 
• 848768-06-9 (R)-3-[2-(benzyloxy)-5-methylphenyl]-N,N-diisopropyl-3-phenylpropan-1-amine 
• 214601-54-4 (R)-[4-benzyloxy-3-(3-diisopropylamino-1-phenyl-propyl)-phenyl]-methanal 
• 156755-37-2 {4-(benzyloxy)-3-[(1R)-3-(dipropan-2-ylamino)-1-phenylpropyl]phenyl}methanol 

Relevant articles and documents

An efficient synthesis of racemic tolterodine

The efficient and cost effective of the synthesis of (±)-tolterodine (1), a precursor of (+)-(R)-tolterodine was efficiently performed from 6-methyl-4-chroman-2-one (2) via 4 steps in high yield. This process is suitable for large-scale commercial production by avoiding hazardous reagents and high pressure of hydrogen gas.

A new efficient route to Tolterodine

Tolterodine, an important urological drug, can be conveniently prepared starting from 1-[2-hydroxy-5-methyl)phenyl]-1-phenylethylene, accessible in high yield by alumina-promoted ortho alkenylation of p-cresol with phenylacetylene. The hydroformylation of this olefin, catalyzed by rhodium complexes both in homogeneous or in aqueous biphasic system, affords the desired linear aldehyde in about 80-90% yield. The reductive amination of this aldehyde, in the presence of HN-(iPr)2 and Pd/C (5%) as the catalytic precursor at 4 atm H2 and 48°C, produces directly tolterodine in more than 90% yield. Some experiments of enantioselective hydroformylation of 1-[2-hydroxy-5-methyl)phenyl]-1-phenylethylene catalyzed by Rh(CO)2acac/(S,R)-Binaphos and other enantiopure ferrocenyldiphosphines afforded only low yields of the expected chiral aldehyde; unfortunately, the achieved ee did not exceed 8%.

The lactol route to fesoterodine: An amine-promoted Friedel-Crafts alkylation on commercial scale

We report the discovery and optimization of an amine-promoted Friedel-Crafts alkylation of cinnamaldehyde with 4-hydroxymethyl phenol. This reaction has been used successfully on commercial scale (200 kg) in the context of the manufacture of fesoterodine, a muscarinic antagonist used for the treatment of overactive bladder. Reductive aminations of diisopropylamine and lactol 4 are also discussed, as well as the resolution of the racemic amine rac-2 into its enantiomerically pure form.

Metal-free annulative hydrosulfonation of propiolate esters: synthesis of 4-sulfonates of coumarins and butenolides

An efficient metal-free and cost-effective method for the synthesis of coumarin and butenolide 4-sulfonates (46 examples) has been developed. The reaction involves addition of sulfonic acids to ethyl propiolates followed by lactonization, resulting in direct formation of coumarin and butenolide 4-sulfonates. This methodology has been elaborated to Sonogashira and Suzuki coupling including the synthesis of rac-tolterodine.

Ligand-Phospholipid Conjugation: A Versatile Strategy for Developing Long-Acting Ligands That Bind to Membrane Proteins by Restricting the Subcellular Localization of the Ligand

We hypothesized that if drug localization can be restricted to a particular subcellular domain where their target proteins reside, the drugs could bind to their target proteins without being metabolized and/or excreted, which would significantly extend the half-life of the corresponding drug-target complex. Thus, we designed ligand-phospholipid conjugates in which the ligand is conjugated with a phospholipid through a polyethylene glycol linker to restrict the subcellular localization of the ligand in the vicinity of the lipid bilayer. Here, we present the design, synthesis, pharmacological activity, and binding mode analysis of ligand-phospholipid conjugates with muscarinic acetylcholine receptors as the target proteins. These results demonstrate that ligand-phospholipid conjugation can be a versatile strategy for developing long-acting ligands that bind to membrane proteins in drug discovery.

PROCESS FOR THE PREPARATION OF (R)-2-(3-DIISOPROPYLAMINO)-1-PHENYLPROPYL)-4METHYLPHENOL AND SALTS THEREOF

The present invention relates to an improved process for the preparation of Tolterodine or salts thereof, which comprises the use of 3-(2-methoxy-5-methylphenyl)-3-phenylpropyl methane sulfonate.

PROCESS FOR PREPARING TOLTERODINE AND THE L-TARTRATE THEREOF

The present invention relates to a process for preparing tolterodine and the L-tartrate thereof. The preparation consists of the following steps: A) ammonolysis reaction between diisopropylamine and compound 2 (3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-

Rearrangement of ethers: A new route to tolterodine

The rearrangement of benzyl phenolic ether in the presence of an acid or AlCl3 is utilized to produce biphenyl methane compounds in very good yields. The synthesis of muscarine receptor antagonist tolterodine is described.

A PROCESS FOR THE PREPARATION OF TOLTERODINE TARTRATE

The present invention relates to provide an improved process for the preparation of tolterodine or salt thereof, comprises a step of reducing 3-(2-methoxy-5-methylphenyl) -3-phenyl propionic acid of formula (III) in the presence of a reducing agent, an acidic reagent and a solvent to obtain 3-(2-methoxy-5-methylphenyl) -3-phenyl propanol of formula (IV).

METHOD OF OBTAINING 3,3-DIPHENYLPROPYLAMINES

The invention relates to a method of obtaining 3,3-diphenylpropylamines (I), wherein R1 is H, alkyl, haloalkyl or alkoxyalkyl, R2 is alkyl, alkoxy, halogen, NO2, CN, CHO, which may be free or protected, CH2OH or COOR6, and R3 and R4 are selected independently from H and alkyl or together with the nitrogen to which they are bound form a ring having 3 to 7 members. The inventive method consists in reacting a propylenephenylamine and a disubstituted aromatic hydrocarbon and, if necessary, separating the desired enantiomer or the mixture of enantiomers, and/or converting the compound (I) into a salt. Compounds (I) are muscarinic receptor antagonists which can be used in the treatment of urinary incontinence and other symptoms of urinary bladder hyperactivity. Said compounds include tolterodine.