93413-77-5

Basic information

• Product Name: 1-(4-Methoxyphenyl)-2-aminoethyl cyclohexanol hydrochloride
• Synonyms: 1-[2-aMino-1-(4-Methoxyphenyl)ethyl]cyclohexan-1-ol;Venlafaxine EP IMpurity C;2-(4-Methoxyphenyl)-2-(1-hydroxycyclohexyl)-ethylamine;1-[2-AMINO-1-(4-METHOXYPHENYL)ETHYL]CYCLOHEXANOL HCL;1-(4-METHOXYPHENYL)-2-AMINOETHYL CYCLOHEXANOL HYDROCHLORIDE;2-(4-METHOXYPHENYL)-2-(1-HYDROXYCYCLOHEXYL)ETHYLAMINE HYDROCHLORIDE;Venlafaxine intermediate; D,L-N,N-Didesmethylvenlafaxine
• CAS NO: 93413-77-5
• Molecular Formula: C₁₅H₂₃NO₂
• Molecular Weight: 249.35
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Velafaxine
• Mol File: 93413-77-5.mol
• Article Data: 29

Chemical Properties

• Melting Point: 172-180°C
• Boiling Point: 394.6 °C at 760 mmHg
• Flash Point: 192.5 °C
• Appearance: pale yellow oil
• Density: 1.107±0.06 g/cm3(Predicted)
• Storage Temp.: Refrigerator
• PKA: 14.75±0.20(Predicted)
• CAS DataBase Reference: 1-(4-Methoxyphenyl)-2-aminoethyl cyclohexanol hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(4-Methoxyphenyl)-2-aminoethyl cyclohexanol hydrochloride(93413-77-5)
• EPA Substance Registry System: 1-(4-Methoxyphenyl)-2-aminoethyl cyclohexanol hydrochloride(93413-77-5)

Safety Data

• Hazardous Substances Data: 93413-77-5(Hazardous Substances Data)

Usage

Synthesis

To a mechanically stirred solution of AlCl3 (103.60 g, 0.779 mol) in THF (900 ml), at 0 oC, LiAlH4 (59.80 g, 1.575 mol) was added cautiously, in portions. Temperature was maintained below 10 oC. A solution of 2-(1-Hydroxycyclohexyl)-2-(4-methoxyphenyl) acetonitrile(130.0 g, 0.530 mol) in THF (500 ml) was added drop-wise over a period of 1.5 hours. The reaction mixture was then brought to room temperature and stirred for 30 minutes. The reaction mixture was again cooled in an ice-salt bath. The reaction was quenched with ethyl acetate (60 ml) maintaining the temperature below 10 oC. The reaction mixture was then transferred to a beaker, cooled externally in an ice-salt bath and treated very cautiously with 25% aq. NaOH solution (360 ml) with mechanical stirring. (After addition of about 50 ml 25% aq. NaOH solution, a hard solid was formed, cooling was removed and the contents were stirred manually during the addition of remaining NaOH solution). The solid was loosened at room temperature, which was further stirred for 1 hour. A bright white solid appeared. The solid was filtered off, washed thoroughly with ethyl acetate. The filtrate was concentrated in vacuo and combined with the above washings, washed with brine, dried over anhydrous Na2SO4, filtered and ethyl acetate removed under reduced pressure to obtain aminoalcohol 38 as a thick yellow oil (129.4 g).

Chemical Properties

Pale Yellow Oil

Definition

ChEBI: A monomethoxybenzene that is the N,N-didesmethyl derivative of venlafaxine.

Upstream product

• 108-94-1 cyclohexanone 
• 469905-08-6 2-(4-methoxy-phenyl)-1-oxa-spiro[2.5]octane-2-carbonitrile 
• 93413-76-4 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol 
• 141-43-5 ethanolamine 
• 130198-05-9 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride 
• 104-47-2 p-methoxybenzylnitrile 
• 1204232-46-1 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol methanesulfonate salt 
• 1336-21-6 ammonium hydroxide 
• 108-93-0 cyclohexanol 

Downstream Products

• 93413-69-5 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol 
• 149289-29-2 N,N-Didesmethyldesvenlafaxine 
• 3698-89-3 dodecyl methyl sulfide 
• 93413-62-8 O-desmethylvenlafaxine 
• 112-55-0 1-dodecylthiol 
• 99300-78-4 venlafaxine hydrochloride 
• 1329795-88-1 (±)-1-{2-[(4-methoxyphenethyl)amino]-1-(4-methoxyphenyl)ethyl}cyclohexanol 
• 93413-90-2 N-Desmethylvenlafaxine hydrochloride 
• 149289-30-5 N-Desmethylvenlafaxine 

Relevant articles and documents

SUBSTITUTED ARYLUREA COMPOUNDS FOR INDUCING APOPTOSIS AND COMPOSITION FOR ANTICANCER COMPRISING THE SAME

The present invention relates to a substituted arylurea compound inducing apoptosis and an anticancer composition comprising the same. The present invention relates to a novel compound capable of preventing, treating and alleviating cancer diseases such as prostate cancer, breast cancer, lung cancer, colorectal cancer, and skin cancer by inhibiting apoptosis of cancer cells and inhibiting proliferation of cancer cells.

Preparation method of venlafaxine impurity E (by machine translation)

The invention belongs to the technical field of organic synthesis, and relates to a preparation method of venlafaxine impurity E, which comprises (1) a condensation reaction, (2) a reduction reaction and (3) a ring-forming reaction. The method for synthesizing venlafaxine impurity E is less in steps, high in product purity, safe in reaction, less in waste liquid, simple in post-treatment, convenient to operate and convenient for industrial production. (by machine translation)

Screening of quinoline, 1,3-benzoxazine, and 1,3-oxazine-based small molecules against isolated methionyl-tRNA synthetase and A549 and HCT116 cancer cells including an in silico binding mode analysis

Elevated activity of methionyl-tRNA synthetase (MRS) in many cancers renders it a possible drug target in this disease area, as well as in a series of parasitic diseases. In the present work, we report the synthesis and in vitro screening of a library of 1,3-oxazines, benzoxazines and quinoline scaffolds against human MRS. Among the compounds tested, 2-(2-butyl-4-chloro-1-(4-phenoxybenzyl)-1H-imidazol-5-yl)-5-(4-methoxyphenyl)-1-oxa-3-azaspiro[5.5]undecane (compound 21) and 2-(2-butyl-4-chloro-1-(4-nitrobenzyl)-1H-imidazol-5-yl)-2,4-dihydro-1H-benzo[d][1,3]oxazine (compound 8) were found to be potent inhibitors of MRS. Additionally, these compounds significantly suppressed the proliferation of A549 and HCT116 cells with IC50 values of 28.4, 17.7, 41.9, and 19.8 μM respectively. Molecular docking studies suggested that the ligand binding orientation overlaps with the original positions of both methionine and adenosine of MRS. This suggests the binding of compound 21 against MRS, which might lead the inhibitory activity towards cancer cells.