230615-51-7

Basic information

• Product Name: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine
• Synonyms: 1-(10-Aza-tricyclo[6.3.1.0]dodeca-2,4,6-trien-10-yl)-2,2,2-trifluoro-ethanone;Ethanone, 2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-1,5-methano-3H-3-benzazepin-3-yl)-;2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine;2-trifluoro-1-(1;5-Methano-3H-3-benzazepin-3-yl)-;5-tetrahydro-1;Ethanone,2,2,2-thrifluoro-1-(1,2,4,5-tetrahydro -1,5-Methano-3H-3-benzapin-3-yl);1-(10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone
• CAS NO: 230615-51-7
• Molecular Formula: C₁₃H₁₂F₃NO
• Molecular Weight: 255.24
• Mol File: 230615-51-7.mol
• Article Data: 6

Chemical Properties

• Melting Point: 67-68 ºC
• Boiling Point: 381.749 °C at 760 mmHg
• Flash Point: 184.675 °C
• Appearance: /
• Density: 1.333
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.528
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: -1.82±0.20(Predicted)
• CAS DataBase Reference: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine(230615-51-7)
• EPA Substance Registry System: 2,3,4,5-Tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine(230615-51-7)

Safety Data

• Hazardous Substances Data: 230615-51-7(Hazardous Substances Data)

Usage

Uses

2,3,4,5-tetrahydro-3-(trifluoroacetyl)-1,5-methano-1H-3-benzazepine is a reactant used in the preparation of Varenicline, a nicotinic α4β2 acetylcholine receptor partial agonist. Aid in smoking cessation.

InChI:InChI=1/C13H12F3NO/c14-13(15,16)12(18)17-6-8-5-9(7-17)11-4-2-1-3-10(8)11/h1-4,8-9H,5-7H2

Upstream product

• 407-25-0 trifluoroacetic anhydride 
• 357425-93-5 1,5-methano-2,3,4,5-tetrahydro-1H-3-benzazepine p-toluenesulfonic acid salt 
• 69718-72-5 10-Aza-tricyclo[6.3.1.02.7]dodeca-2⁽⁷⁾,3,5-triene 
• 230615-52-8 2,3,4,5-tetrahydro-1,5-methylene-1H-3-benzazepine hydrochloride 

Downstream Products

• 230615-59-5 1-(7,8-dinitro-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)-2,2,2-trifluoroethanone 
• 230615-53-9 1-(4-nitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone 

Relevant articles and documents

PROCESS FOR PREPARING VARENICLINE, VARENICLINE INTERMEDIATES, AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

Provided herein is an improved, convenient, commercially viable and environmentally friendly process for the preparation of varenicline or a pharmaceutically acceptable salt thereof comprising reacting l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien- 10-yl)-2,2,2-trifluoro-ethanone with chloroacetaldehyde in the pressence of an oxygen source. Provided further herein is an improved and industrially advantageous process for the preparation of l-(4,5-diamino-10-aza-tricyclo[6.3.1.02 7]dodeca-2(7),3,5-trien-10-yl)-2,2,2- trifluoro-ethanone.

PROCESSES FOR THE PREPARATION OF VARENICLINE AND INTERMEDIATES THEREOF

The invention provides an improved process for the preparation and purification of Varenicline and intermediates for the preparation of Varenicline.

Process for the preparation of 1,3-substituted indenes and aryl-fused azapolycyclic componunds

The present invention relates to processes for the preparation of any of the intermediate 1,3-substituted indenes of the formulae (Ia), (Ib) and (Ic) or a mixture thereof: wherein R1, R2, R3, R4, and R5 are defined herein. Compounds of formulae (Ia), (Ib) and (IC) or mixtures thereof are useful in the preparation of compounds of formula (II): wherein R2, R3 and R6 are also defined herein.