230615-69-7

Basic information

• Product Name: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine-7,8-diamine
• Synonyms: 1-(4,5-Diamino-10-aza-tricyclo[6.3.1.0]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanone;1,5-Methano-1H-3-benzazepine-7,8-diamine, 2,3,4,5-tetrahydro-3-(trifluoroacetyl)- (9CI);1-(7,8-diamino-1,2,4,5-tetrahydro-1,5-methano-3H-3-benzazepin-3-yl)-2,2,2-trifluoroethanone;2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine-7,8-diamine;1-(7,8-diaMino-4,5-dihydro-1H-1,5-Methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone;Ethanone,1-(7,8-diamino-1,2,4,5-tetrahydro-1,5-methano-3H-3-benzazepin-3-yl)-2,2,2-trifluoro-
• CAS NO: 230615-69-7
• Molecular Formula: C13H14F3N3O
• Molecular Weight: 285.26
• Product Categories: Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 230615-69-7.mol
• Article Data: 13

Chemical Properties

• Melting Point: 83-88°C
• Boiling Point: 487.739 °C at 760 mmHg
• Flash Point: 248.776 °C
• Appearance: Brownish orange solid
• Density: 1.455
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.604
• Storage Temp.: Refrigerator, Under Inert Atmosphere
• Solubility: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• PKA: 4.86±0.20(Predicted)
• CAS DataBase Reference: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine-7,8-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine-7,8-diamine(230615-69-7)
• EPA Substance Registry System: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine-7,8-diamine(230615-69-7)

Safety Data

• Hazardous Substances Data: 230615-69-7(Hazardous Substances Data)

Usage

Uses

Varenicline intermediate.

InChI:InChI=1/C13H14F3N3O/c14-13(15,16)12(20)19-4-6-1-7(5-19)9-3-11(18)10(17)2-8(6)9/h2-3,6-7H,1,4-5,17-18H2

Upstream product

• 230615-59-5 1-(7,8-dinitro-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone 

Downstream Products

• 230615-70-0 1-(5,8,14-triazatetracyclo[10.3.1.0^2,11.0^4,9]hexadeca-2,4,6,8,10-pentaen-4-yl)-2,2,2-trifluoroethanone 
• 230615-70-0 1-(9,10-dihydro-6H-6,10-methanoazepino[4,5-g]quinoxaline-8(7H)-yl)-2,2,2,-trifluoroethanone 
• 357426-10-9 C₁₅H₁₂F₃N₃O₂ 

Relevant articles and documents

Varenicline: An α4β2 nicotinic receptor partial agonist for smoking cessation

Herein we describe a novel series of compounds from which varenicline (1, 6,7,8,9-tetrahydro-6,10-methano-6H-pyrazino[2,3-h][3]benzazepine) has been identified for smoking cessation. Neuronal nicotinic acetylcholine receptors (nAChRs) mediate the dependence-producing effects of nicotine. We have pursued α4β2 nicotinic receptor partial agonists to inhibit dopaminergic activation produced by smoking while simultaneously providing relief from the craving and withdrawal syndrome that accompanies cessation attempts. Varenicline displays high α4β2 nAChR affinity and the desired in vivo dopaminergic profile.

Hydrogenation of a pharmaceutical intermediate by a continuous stirred tank reactor system

A proof of concept study on the continuous hydrogenation of a pharmaceutical intermediate is presented. A slurry feed of CP- 548495, a dintro intermediate in a smoking cessation drug, was reduced in a two-reactor continuous stirred tank train to the diami

Preparation method of vanniklan tartrate tablets degraded impurities

The present invention proposes a method for the preparation of the degradation of impurities in the tartaric acid vareniclan tablets, with ammonium formate as a hydrogen donor, the dinitrolate is reduced under the palladium carbon catalyzed to obtain a diamidylation, the diaminolide and the aqueous solution of glyal are cyclic reaction to obtain a cyclic product, and then the cyclic product is hydrolyzed under the action of sodium hydroxide, the trifluoroacetyl group is removed to obtain a free base, and finally the free base is reacted with chloroacetic acid under the action of the alkali, and the solvent is evaporated after the end of the reaction, Add water to dissolve and adjust the pH until the solids precipitate from the aqueous phase, collect and filter the solids to dry to obtain acetic acid adducts. The present invention fills the technical gap of the current impurity preparation method, the prepared high-purity impurities can be applied as a control sample to the pharmaceutical impurity research and production quality control process of varenicline tartrate, providing a guarantee for the comprehensive quality control of the varenicline tartrate API.

AN IMPROVED PROCESS FOR THE PREPARATION OF VARENICLINE AND SALT THEREOF

of the Invention The present invention relates to an improved process for the preparation of varenicline and salt thereof. The present invention also provides a process for the 2,7preparation of l-(4,5-dinitro-10-aza-tricyclo[6.3.1.0 ]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoroethanone of Formula 4 using ethyl trifluoroacetate and further converted to varenicline and salt thereof.