93413-76-4

Usage

Synthesis

A mixture of p-methoxyphenylacetonitrile 36 (100 g, 0.68 mol), 10% aqueous NaOH solution (100 ml, 0.25 mol) and TBAHSO4 (5 g, 0.014 mol) was stirred at room temperature for 30 minutes. A dark red colour appeared. To this was added cyclohexanone 34 (67 g, 0.680 mol) in small portions at 0 oC, with vigorous stirring, in such a way that temperature should not rise above 10 oC. A white solid was formed within 30 minutes to one hour. The solid was crushed and the reaction mixture was further stirred vigorously at room temperature for one more hour. The solid was filtered, washed with water till neutral to pH paper and air-dried. Crystallization from ethyl acetatepetroleum ether (500:350, v/v) gave a bright white solid (161.66 g).

Chemical Properties

White Powder

InChI:InChI=1/C15H19NO2/c1-18-13-7-5-12(6-8-13)14(11-16)15(17)9-3-2-4-10-15/h5-8,14,17H,2-4,9-10H2,1H3

Upstream product

• 108-94-1 cyclohexanone 
• 874-90-8 4-methoxybenzonitrile 
• 104-47-2 p-methoxybenzylnitrile 
• 108-93-0 cyclohexanol 

Downstream Products

• 149289-30-5 N-Desmethylvenlafaxine 
• 93413-77-5 N,N-didesmethylvenlafaxine 
• 130198-05-9 1-[2-amino-1-(4-methoxyphenyl)ethyl]cyclohexanol hydrochloride 
• 149289-29-2 N,N-Didesmethyldesvenlafaxine 
• 93413-90-2 N-Desmethylvenlafaxine hydrochloride 
• 272788-07-5 N-[2-(1-hydroxycyclohexyl)-2-(4-methoxyphenyl)ethyl]formamide 

Relevant academic research and scientific papers

Method for industrially producing venlafaxine hydrochloride

The invention discloses a method for industrially producing venlafaxine hydrochloride, and relates to the technical field of drug organic synthesis. The method has the advantages of easily available raw materials of the whole synthetic route, mild reaction conditions, simple and convenient operation, high yield, environment friendliness and good repeatability of the preparation method, and can be used for preparing venlafaxine hydrochloride with high yield and high purity.

Preparation method of venlafaxine amine impurity

The invention discloses a preparation method of a venlafaxine amine impurity, and relates to the technical field of organic synthesis of medicines. P-methoxybenzyl cyanide and cyclohexanone are used as starting raw materials, condensation reaction is performed under the action of a phase transfer catalyst and alkali to obtain a compound 1, dehydration reaction is performed on the compound 1 under the action of acid to obtain a compound 2, and reduction reaction is conducted on the compound 2 under the action of a reducing agent to obtain an amine impurity I. The venlafaxine amine impurity (amine impurity I) with the structure is disclosed and successfully synthesized firstly, the purity of the venlafaxine amine impurity reaches 99% or above, and a high-purity impurity reference substance is provided for detection and content control of the impurity in venlafaxine hydrochloride medicine.

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)

Method for preparing pharmaceutical intermediate with hydrotalcite material by catalysis

The invention belongs to the technical field of medicine, and particularly relates to a method for preparing a pharmaceutical intermediate with a hydrotalcite material by catalysis. The method includes first utilizing lithium fluoride as a modifier to modify the Zn/Al hydrotalcite material to obtain a hydrotalcite-supported lithium fluoride material. The hydrotalcite-supported lithium fluoride material can catalyze 4-methoxybenzyl cyanide and cyclohexanone to have condensation reaction to prepare 1-hydroxycyclohexyl-4-methoxybenzyl cyanide. The defects in the prior art of harsh reaction conditions, low yield and high environment pollution in the preparation process of overcomes the harsh reaction conditions in the preparation of a PRISTIQ and/or venlafaxine framework are overcome.

Selective Hydrogenation of Nitriles to Primary Amines Catalyzed by a Polysilane/SiO2-Supported Palladium Catalyst under Continuous-Flow Conditions

Hydrogenation of nitriles to primary amines with heterogeneous catalysts under liquid-phase continuous-flow conditions is described. Newly developed polysilane/SiO2-supported Pd was found to be an effective catalyst and various nitriles were converted into primary amine salts in almost quantitative yields under mild reaction conditions. Interestingly, a complex mixture was obtained under batch conditions. Lifetime experiments showed that this catalyst remained active for more than 300 h (TON≥10 000) without loss of selectivity and no metal leaching from the catalyst occurred. By using this continuous-flow hydrogenation, synthesis of venlafaxine, an antidepressant drug, has been accomplished.

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.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF DEPRESSION

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for treating or preventing depression may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of major depressive disorder (MDD), anxiety, neurological diseases, general anxiety disorder, social phobia, panic disorder, vasomotor symptoms, diabetic neuropathy, epilepsy, bipolar disorder, migraine, schizophrenia, cancer, menopause, HIV and familial adenomatous polyposis.

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.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF DEPRESSION

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for treating or preventing depression may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of major depressive disorder (MDD), anxiety, neurological diseases, general anxiety disorder, sodal phobia, panic disorder, vasomotor symptoms, diabetic neuropathy, epilepsy, bipolar disorder, migraine, schizophrenia, cancer, menopause, HIV and familial adenomatous polyposis.