42142-52-9

Basic information

• Product Name: 3-Hydroxy-N-methyl-3-phenyl-propylamine
• Synonyms: ALPHA-(2-METHYLAMINO)-ETHYLBENZENEMETHANOL;ALPHA-[2-(METHYLAMINO)ETHYL]BENZYL ALCOHOL;3-HYDROXY-N-METHYL-3-PHENYLPROPYLAMINE;3-METHYLAMINO-1-PHENYLPROPANOL;3-(METHYLAMINO)-1-PHENYLPROPAN-1-OL;3-METHYLAMINO-1-PHENYL-1-PROPANOL;N-METHYL-3-PHENYL-3-HYDROXYPROPYLAMINE;N-METHYL-3-HYDROXY-3-PHENYL PROPYLAMINE
• CAS NO: 42142-52-9
• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23
• EINECS: 255-679-8
• Product Categories: INTERMEDIATESOFFLUOXETINE;Intermediates of Fluoxetine;Amino Alcohols;Organic Building Blocks;Oxygen Compounds;Amino Alcohols;Building Blocks;Chemical Synthesis;Organic Building Blocks;Oxygen Compounds
• Mol File: 42142-52-9.mol

Chemical Properties

• Melting Point: 64 °C
• Boiling Point: 170 °C / 31mmHg
• Flash Point: 114.8 °C
• Appearance: /
• Density: 1.017 g/cm³
• Vapor Pressure: 0.00126mmHg at 25°C
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: DMSO (Soluble), Methanol (Slightly)
• PKA: 14.24±0.20(Predicted)
• CAS DataBase Reference: 3-Hydroxy-N-methyl-3-phenyl-propylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Hydroxy-N-methyl-3-phenyl-propylamine(42142-52-9)
• EPA Substance Registry System: 3-Hydroxy-N-methyl-3-phenyl-propylamine(42142-52-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36/37
• WGK Germany: 3
• Hazardous Substances Data: 42142-52-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
3-Hydroxy-N-methyl-3-phenyl-propylamine is used as an initiator in radical addition reactions with tetrahalomethanes. Its ability to initiate these reactions makes it a valuable compound in the synthesis of various organic compounds, particularly in the pharmaceutical and chemical industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 3-Hydroxy-N-methyl-3-phenyl-propylamine is used as an impurity in fluoxetine (F597100). As an impurity, it is important to monitor and control its presence in the final product to ensure the safety, efficacy, and quality of the medication.
Used in Research and Development:
3-Hydroxy-N-methyl-3-phenyl-propylamine is also used in research and development for the study of its chemical properties and potential applications. Researchers may explore its use in the synthesis of new compounds or as a precursor in the development of novel pharmaceuticals.

InChI:InChI=1/C10H15NO/c1-11-8-7-10(12)9-5-3-2-4-6-9/h2-6,10-12H,7-8H2,1H3/p+1/t10-/m1/s1

Upstream product

• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 74-89-5 methylamine 
• 27152-62-1 3-(N-methylamino)propiophenone 
• 21970-65-0 3-(benzyl-methyl-amino)-1-phenylpropan-1-one 
• 2538-50-3 β-Methylaminoethyl phenyl ketone hydrochloride 
• 98-86-2 acetophenone 
• 936-59-4 3-chloropropiophenone 
• 877-50-9 3-(methylamino)-1-phenylprop-2-en-1-one 
• 68408-65-1 2-methyl-5-phenyl-isoxazolidine 
• 5409-62-1 3-(benzyl methylamino)-1-phenylpropan-1-one hydrochloride 
• 62872-58-6 3-iodo-1-phenyl-propan-1-ol 
• 104-55-2 3-phenyl-propenal 
• 108606-85-5 N-[(3-phenylprop-2-en)methylene]-α-phenylbenzenemethanamine 
• 768-03-6 Phenyl vinyl ketone 

Downstream Products

• 19798-87-9 tetrahydro-3-methyl-6-phenyl-2H-1,3-oxazine 
• 1939-17-9 N-<3-Phenyl-propin-(2)-yl>-N-<3-hydroxy-3-phenyl-propyl>-methylamin 
• 244059-08-3 tert-butyl N-(3-hydroxy-3-phenylpropyl)-N-methylcarbamate 
• 28075-29-8 N-methyl-3,3-diphenylpropylamine 
• 100-52-7 benzaldehyde 
• 98-88-4 benzoyl chloride 
• 98-86-2 acetophenone 
• 768-03-6 Phenyl vinyl ketone 
• 244059-09-4 rac-3-(N-methyl-N-(tert-butyloxycarbonyl)amino)-1-phenylpropylamine 
• 1047644-75-6 1,1-dimethylethyl [3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenylpropyl]methylcarbamate 
• 693262-07-6 (+/-) ethyl 3-[N-methyl-N-(3-hydroxy-3-phenylpropyl)]aminopropionate 
• 871351-42-7 trifluoroacetic acid 3-[methyl-(2,2,2-triffuoro-acetyl)-amino]-1-phenyl-propyl ester 

Relevant articles and documents

Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis

Controlling the selectivity in a hydroamination reaction is an extremely challenging yet highly desirable task for the diversification of amines. In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth's abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful hydroamination with primary and secondary allylic alcohols with excellent functional group tolerance (57 examples). The catalysis could be performed on a gram scale and has been applied for the synthesis of drug molecules. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.

Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients

Systems and methods for synthesizing chemical products, including active pharmaceutical ingredients, are provided. Certain of the systems and methods described herein are capable of manufacturing multiple chemical products without the need to fluidically connect or disconnect unit operations when switching from one making chemical product to making another chemical product.

Convenient Continuous Flow Synthesis of N-Methyl Secondary Amines from Alkyl Mesylates and Epoxides

The first continuous flow process was developed to synthesize N-methyl secondary amines from alkyl mesylates and epoxides via a nucleophilic substitution using aqueous methylamine. A variety of N-methyl secondary amines were produced in good to excellent yields, including a number of bioactive compounds or their precursors. Up to 10.6 g (88% yield) of an N-methyl secondary amine was produced in 140 min process time. The amination procedure included an in-line workup, and the starting mesylate material was also produced in continuous flow from the corresponding alcohol. Finally, an in-line process combining the mesylate synthesis and nucleophilic substitution was developed.

R-(-)-atomoxetine hydrochloride preparation method

The invention provides an R-(-)-atomoxetine hydrochloride preparation method, which comprises: preparing 3-methylamino-1-phenyl-1-propanol by using 1-phenyl-2-propenyl-1-one as a starting raw material, carrying out etherification on the 3-methylamino-1-phenyl-1-propanol and o-halo toluene in an inorganic alkali environment, splitting with L-(+)-mandelic acid to obtain R-(-)-tomoxetine-S-(+)-mandelate, refining the R-(-)-tomoxetine-S-(+)-mandelate, and carrying out hydrochloride forming to obtain the R-(-)-atomoxetine hydrochloride. According to the present invention, the method eliminates theoxalate refining step so as to reduce the reaction step, has advantages of cheap and easily available raw materials, less side reactions, low toxicity of the reaction solvent, high yield, high purity,low cost and the like, and is suitable for industrial production.

A model target anti-tumor medicament and its preparation method and application (by machine translation)

This invention relates to the targeting of antineoplastic eEF2K of a small molecule inhibitor, its formula (I), formula (II) the structure of the formula (III): Formula (I), formula (II) compound of the formula (III) structure and its pharmaceutically acceptable salt thereof can kill cancer cells, the healthy organism cells are not affected, to various tumor is markedly inhibited, in particular breast cancer, glioma, stomach cancer, liver cancer cells is markedly inhibited. (by machine translation)

Controlling the exothermicity of O-arylation by evaporative cooling during the process development of fluoxetine hydrochloride

This study illustrates the optimization of the O-arylation step of fluoxetine hydrochloride (1) synthesis. In the entire process, this is the most critical step that dictates the yield and quality of the product. The highlight of the process is the concept of evaporative cooling that was employed in manipulating the above highly exothermic reaction by introducing toluene as the cosolvent. The evaporative cooling not only aided in getting an efficient procedure but also increased the yield of 1 and simplified the work-up procedure. This was a protective approach adopted for process safety, considering the worst-case scenario in the plant.

SUBSTITUTED 3-HETEROARYLOXY-3-(HETERO)ARYL-PROPYLAMINES AS SEROTONIN TRANSPORTER AND SEROTONIN HT2C RECEPTOR MODULATORS

The present invention relates to compounds compound according to Formula (1): and pharmaceutically acceptable salts, hydrates and solvates thereof. These compounds have serotonin (5-HT) transporter inhibitory effects and 5-HT 2C receptor antagonist or inverse agonist effects. The present invention also relates to pharmaceutical compositions comprising these compounds, and methods of using them for application in the prophylaxis or treatment of CNS disorders.

Total synthesis of fluoxetine and duloxetine through an in situ imine formation/borylation/transimination and reduction approach

We report efficient, catalytic, asymmetric total syntheses of both (R)-fluoxetine and (S)-duloxetine from α,β-unsaturated aldehydes conducting five sequential one-pot steps (imine formation/copper mediated β-borylation/transimination/reduction/oxidation) followed by the specific ether group formation which deliver the desired products (R)-fluoxetine in 45% yield (96% ee) and (S)-duloxetine in 47% yield (94% ee). This journal is the Partner Organisations 2014.

Preparation of fluoxetine by multiple flow processing steps

Microflow technology is established as a modern and fashionable tool in synthetic organic chemistry, bringing great improvement and potential, on account of a series of advantages over flask methods. The study presented here focuses on the application of flow chemistry process in performing an efficient multiple step syntheses of (±)-fluoxetine as an alternative to conventional synthetic methods, and one of the few examples of total synthesis accomplished by flow technique.

Design, synthesis and evaluation of substituted N-(3-arylpropyl)-9,10- dihydro-9-oxoacridine-4-carboxamides as potent MDR reversal agents in cancer

A novel class of molecules with structure N-(3-arylpropyl)-9,10-dihydro-9- oxoacridine-4-carboxamides (20-29) were designed by generating a pharmacophore for potent MDR reversal activity using phase drug design software. The designed molecules were synthesized by a novel synthesis route and evaluated for their inhibitory effects on the transport activity of P-glycoprotein (P-gp) by standard Hoechst 33342 assay method. Based on the pIC50 values of ten title compounds screened, three compounds exhibited better activity as compared to Verapamil used as standard.