272788-00-8

Basic information

• Product Name: R-VENLAFAXINE-DI-P-TOLUOYL-D-TARTRATE SALT
• Synonyms: R-VENLAFAXINE-DI-P-TOLUOYL-D-TARTRATE SALT;1-[(1R)-2-(Dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexanol (2S,3S)-2,3-Bis[(4-methylbenzoyl)oxy]butanedioate Salt
• CAS NO: 272788-00-8
• Molecular Formula: C37H45NO10
• Molecular Weight: 663.7539
• Product Categories: Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 272788-00-8.mol
• Article Data: 4

Chemical Properties

• Melting Point: 120-122°C
• Boiling Point: 824.7°C at 760 mmHg
• Flash Point: 452.6°C
• Appearance: /
• Vapor Pressure: 8.4E-29mmHg at 25°C
• Solubility: Methanol, Water
• CAS DataBase Reference: R-VENLAFAXINE-DI-P-TOLUOYL-D-TARTRATE SALT(CAS DataBase Reference)
• NIST Chemistry Reference: R-VENLAFAXINE-DI-P-TOLUOYL-D-TARTRATE SALT(272788-00-8)
• EPA Substance Registry System: R-VENLAFAXINE-DI-P-TOLUOYL-D-TARTRATE SALT(272788-00-8)

Safety Data

• Hazardous Substances Data: 272788-00-8(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

(-)-Venlafaxine derivative as inhibitor of neuronal monoamine reuptake.

InChI:InChI=1/C20H18O8.C17H27NO2/c1-11-3-7-13(8-4-11)19(25)27-15(17(21)22)16(18(23)24)28-20(26)14-9-5-12(2)6-10-14;1-18(2)13-16(17(19)11-5-4-6-12-17)14-7-9-15(20-3)10-8-14/h3-10,15-16H,1-2H3,(H,21,22)(H,23,24);7-10,16,19H,4-6,11-13H2,1-3H3/t15-,16-;16-/m00/s1

Upstream product

• 32634-66-5 Di-p-toluoyl-L-tartaric acid 
• 93413-69-5 1-[2-dimethylamino-1-(4-methoxyphenyl)ethyl]cyclohexanol 
• 99300-78-4 venlafaxine hydrochloride 
• 93413-44-6 (R)-1-[2-(dimethylamino)-1-(4-methoxyphenyl)ethyl]cyclohexan-1-ol 
• 32634-68-7 (2S,3S)-di-4-toluoyltartaric acid 

Downstream Products

• 93413-45-7 (+)-Venlafaxine hydrochloride 
• 1049700-94-8 (-)-O-desmethylvenlafaxine hydrochloride 
• 142761-11-3 (R)-4-(2-(dimethylamino)-1-(1-hydroxycyclohexyl)ethyl)phenol 

Relevant articles and documents

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.

SOLID FORMS COMPRISING (-) O-DESMETHYLVENLAFAXINE AND USES THEREOF

Solid forms comprising a compound useful in the treatment, prevention and management of various conditions and diseases are provided herein. In particular, the invention provides solid forms comprising (-)-O-desmethylvenlafaxine, including salts thereof, having utility for the treatment, prevention and management of conditions 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.