149289-29-2

Basic information

• Product Name: 1-[2-amino-1-(4-hydroxyphenyl)ethyl]cyclohexanol
• Synonyms: O-Desmethyl-N,N-didesmethylvenlafaxine;Tridesmethylvenlafaxine;D,L-N,N-DidesMethyl-O-desMethyl Venlafaxine;4-[2-amino-1-(1-hydroxycyclohexyl)ethyl]phenol;Desvenlafaxine N,N-Didesmethyl Imp
• CAS NO: 149289-29-2
• Molecular Formula: C₁₄H₂₁NO₂
• Molecular Weight: 235.32204
• EINECS: 1533716-785-6
• Mol File: 149289-29-2.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 405.0±20.0 °C(Predicted)
• Appearance: /
• Density: 1.179
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 9.72±0.26(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: 1-[2-amino-1-(4-hydroxyphenyl)ethyl]cyclohexanol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-amino-1-(4-hydroxyphenyl)ethyl]cyclohexanol(149289-29-2)
• EPA Substance Registry System: 1-[2-amino-1-(4-hydroxyphenyl)ethyl]cyclohexanol(149289-29-2)

Safety Data

• Hazardous Substances Data: 149289-29-2(Hazardous Substances Data)

Usage

Uses

D,L-N,N-Didesmethyl-O-desmethyl Venlafaxine is a metabolite of Venlafaxine (V120000), a selective serotonin noradrenaline reuptake inhibitor. Used as an antidepressant.

Upstream product

• 26960-77-0 sodium dodecanethiolate 
• 93413-77-5 N,N-didesmethylvenlafaxine 
• 14191-95-8 4-cyanomethylphenol 
• 104-47-2 p-methoxybenzylnitrile 
• 108-94-1 cyclohexanone 
• 93413-76-4 1-[cyano(4-methoxyphenyl)methyl]cyclohexanol 
• 130198-05-9 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride 

Downstream Products

• 93413-62-8 O-desmethylvenlafaxine 
• 1076199-24-0 tert-butyl 2-(4-(benzyloxy)phenyl)-2-(1-hydroxycyclohexyl)carbamate 
• 1168135-16-7 1-[2-amino-1-(4-benzyloxyphenyl)ethyl]cyclohexanol 

Relevant articles and documents

Synthesis method of venlafaxine

The invention relates to the technical field of drug synthesis, in particular to a synthesis method of venlafaxine. The synthesis method comprises first steps of using p-hydroxyphenylacetonitrile as a raw material, adding an activator under anhydrous conditions, and reacting with cyclohexanone to obtain 2 -cyclohexylene -2 - (4 hydroxybenzene) acetonitrile. 2nd-Step: 2 - Cyclohexylene -2 - (4 hydroxybenzene) acetonitrile was oxidized with peracetic acid to give an epoxy compound. 3rd: The epoxy compound is added with catalyst Raney nickel, potassium hydroxide assisted catalysis and high pressure hydrogenation to obtain amino. 4th: The amino is then reacted Eschweiler-Clarke, i.e. the amino is reacted with a - formaldehyde system in formic acid to give a desvenlafaxine. The method has the advantages of high environmental friendliness, low production cost, simple steps, mild reaction conditions and high total yield of 74% or more, and is suitable for large-scale industrial production.

DERIVATIVES OF (-)-VENLAFAXINE AND METHODS OF PREPARING AND USING THE SAME

Methods of preparing, and compositions comprising, derivatives of (?)-venlafaxine are disclosed. Also disclosed are methods of treating and preventing diseases and disorders including, but not limited to, affective disorders such as depression, bipolar and manic disorders, attention deficit disorder, attention deficit disorder with hyperactivity, Parkinson's disease, epilepsy, cerebral function disorders, obesity and weight gain, incontinence, dementia and related disorders.

PROCESS FOR SYNTHESIZING DESVENLAFAXINE FREE BASE AND SALTS OR SOLVATES THEREOF

The invention relates generally to an improved process for manufacturing desvenlafaxine free base and salts or solvates thereof.