93413-45-7

Basic information

• Product Name: (+)-Venlafaxine hydrochloride
• Synonyms: (+)-Venlafaxine hydrochloride
• CAS NO: 93413-45-7
• Molecular Weight: 313.868
• Mol File: 93413-45-7.mol

Chemical Properties

• CAS DataBase Reference: (+)-Venlafaxine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Venlafaxine hydrochloride(93413-45-7)
• EPA Substance Registry System: (+)-Venlafaxine hydrochloride(93413-45-7)

Safety Data

• Hazardous Substances Data: 93413-45-7(Hazardous Substances Data)

Upstream product

• 111-24-0 1,5-dibromo-pentane 
• 909398-05-6 methyl 3-N,N-dimethylamino-(2S)-(4-methoxyphenyl)propionate 
• 272788-00-8 2C₁₇H₂₇NO₂*C₂₀H₁₈O₈ 
• 93413-69-5 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol 
• 99300-78-4 venlafaxine hydrochloride 
• 93413-46-8 (S)-1-(2-(dimethylamino)-1-(4-methoxyphenyl)ethyl)cyclohexanol 

Relevant articles and documents

Enantioselective Synthesis of α-Aryl-β2-Amino-Esters by Cooperative Isothiourea and Br?nsted Acid Catalysis

The synthesis of α-aryl-β2-amino esters through enantioselective aminomethylation of an arylacetic acid ester in high yields and enantioselectivity via cooperative isothiourea and Br?nsted acid catalysis is demonstrated. The scope and limitatio

Efficient resolution of venlafaxine and mechanism study via X-ray crystallography

Numbers of resolving factors were investigated to improve resolution of venlafaxine 1. An effective resolving agent, O,O′-di-p-toluoyl-(R, R)-tartaric acid 2, was screened using similar method of ‘Dutch resolution’ from tartaric acid derivatives. The resolution efficiency was up to 88.4%, when the ratio of rac-1 and 2 was 1:0.8 in THF with little water (10:1?v/v). Enantiomerically pure venlafaxine was prepared with 99.1% ee in 82.2% yield. The chiral resolution mechanism was first explained through X-ray crystallographic study. One diastereomeric salt with well solubility forms a columnar supramolecular structure as the acidic salt (R)-1·2, while the other diastereomeric salt with less solubility forms a multilayered sandwich supramolecular structure by enantio-differentiation self-assembly as the neutral salt 2(S)-1·2. The water molecules play a key role in the optical resolution, as indicated by the special structures of the diastereomeric salts.

Process for selective synthesis of enantiomers of substituted 1-(2-amino-1-phenyl-ethyl)-cyclohexanols

A process for the enantioselective synthesis of an (S)— or (R)-1-[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol and analogues or salt thereof are described. The method involves the steps of (a) reacting an (S) or (R) 4-benzyloxazolidinone with a mixed anhydride of a methyoxyphenylacetic acid under conditions which form a oxazolidinone, (4S)— or (4R)-4-benzyl-3-[methyoxyphenyl]acetyl]-oxazolidin-2-one, (b) treating the (4S)— or (4R)-4-benzyl-3-[(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one with an aprotic amine base and titanium chloride in a chlorinated solvent under conditions which permit formation of the corresponding anion, (c) mixing the corresponding anion with titanium chloride and cylcohexanone under conditions which permit an aldol reaction to form the corresponding (4S)— or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one, (d) hydrolyzing the (4S)— or (4R)-4-benzyl-3-[(2R)-2-(1-hydroxycyclohexyl)-2-(methoxyphenyl)acetyl]-1,3-oxazolidin-2-one to form a chiral acid (2S or 2R)-(1-hydroxycyclohexyl)-methoxyphenyl)acetic acid, (e) coupling the chiral phenylacid to a secondary amine to form an amide, and (f) reducing the amide to form an (S) or (R) 1[2-dimethylamino)-1-(methoxyphenyl)ethyl]cyclohexanol or a salt thereof.