177793-79-2

Basic information

• Product Name: (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxaMide
• Synonyms: (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxaMide;[S-(R*,R*)]-N-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxaMide;Palonosetron Impurity 4;(1S)-N-[(3S)-1-azabicyclo[2.2.2]octan-3-yl]-1,2,3,4-tetrahydronaphthalene-1-carboxamide
• CAS NO: 177793-79-2
• Molecular Formula: C18H24N2O
• Molecular Weight: 284
• EINECS: 1592732-453-0
• Product Categories: Amines;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 177793-79-2.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 495.3±34.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 14.98±0.20(Predicted)
• Stability: Hygrosocpic
• CAS DataBase Reference: (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxaMide(CAS DataBase Reference)
• NIST Chemistry Reference: (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxaMide(177793-79-2)
• EPA Substance Registry System: (1S)-N-(3S)-1-Azabicyclo[2.2.2]oct-3-yl-1,2,3,4-tetrahydro-1-naphthalenecarboxaMide(177793-79-2)

Safety Data

• Hazardous Substances Data: 177793-79-2(Hazardous Substances Data)

Upstream product

• 1914-65-4 tetralin-1-carboxylic acid 
• 120570-05-0 (S)-3-aminoquinuclidine 
• 85977-52-2 (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 6530-09-2 (S)-1-azabicyclo[2.2.2]oct-3-ylamine dihydrochloride 
• 50341-99-6 1,2,3,4-tetrahydronaphthalene-1-carbonyl chloride 

Downstream Products

• 135729-60-1 palonosetron 
• 177793-80-5 C₁₈H₂₆N₂ 
• 135755-51-0 palonosetron hydrochloride 
• 177793-80-5 (1-azabicyclo[2.2.2]oct-3-yl)-(1,2,3,4-tetrahydronaphthalen-1-ylmethyl)amine 

Relevant articles and documents

Method for the preparation of high purity Palonosetron intermediates

The present invention relates to a method for manufacturing a high purity palonosetron intermediate compound represented by chemical formula 1. The present invention provides a method for manufacturing N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalen-1-ylcarboxamide, represented by chemical formula 1 with a high purity by conducting a reaction with a compound of chemical formula 2, which is a racemic mixture, under conditions of an inorganic base and a mixed solvent.COPYRIGHT KIPO 2020

Preparation method of high-purity palonosetron hydrochloride

The invention discloses a preparation method of high-purity palonosetron hydrochloride. A synthesis method is as follows: taking 1,2,3,4-tetrahedro-naphthoic acid as a starting raw material, taking quinine as a resolving agent to obtain chiral(S)-1,2,3,4-tetrahedro-naphthoic acid, acylating the chiral(S)-1,2,3,4-tetrahedro-naphthoic acid by using oxalyl chloride, and then reacting with (S)-3-aminoquinuclidine ammonia salt to obtain amide compound; concentrating, adding water to dilute, adding alkali to adjust pH value to obtain (R)-N-((S)-3-quinine)-1,2,3,4-tetralyl-1-formamide; performing reduction reaction on an intermediate under the existence of the sodium borohydride and boron trifluoride diethyl etherate so as to obtain (R)-N-(1-((S)-1,2,3,4-tetralyl)methyl)-3-quinine amine, continuously reacting with the triphosgene and boron trifluoride diethyl etherate, salting, extracting and regulating the pH value to obtain a crude product of the Palonosetron after the reaction is completed; and salting and refining the crude product in isopropanol so as to obtain the Palonosetron Hydrochloride with high purity. The preparation method not only solves the problem that the palonosetron hydrochloride is low in yield and unstable in process for a long time, but also adopts class-three solvent ethyl acetate to extract in the synthesis of each step, the invention is in favor of the environmental protection, and convenient for solvent recycling and cost saving, and is suitable for industrial production.

A hydrochloric acid palonosetron synthesis method

The invention relates to a new synthetic method of palonosetron hydrochloride, and belongs to the field of pharmaceutical organic synthesis. The synthetic method adopts racemized tetrahydro naphthoic acid as a raw material; a reaction is carried out with thionyl chloride and (S)-3-aminoquinuclidine; after repeated washing, (S,S)-quinuclidine tetrahydronaphthalene carboxamide is obtained; the amide is reacted with sodium borohydride and boron trifluoride diethyl etherate; the product is added into a hydrochloric acid aqueous solution to obtain the palonosetron hydrochloride. According to the method, in the amide synthetic process, ethyl acetate is used as a solvent, which reduces the generation of by-products. In addition, according to the method, in the post-treatment process, impurities are removed by phase transfer, which increases product optical purity; through repeated washing, other impurities generated in the reaction are removed, and high-purity product is obtained.