135729-73-6

Basic information

• Product Name: 1H-Benz[de]isoquinolin-1-one,2-(3S)-1-azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-,(3aR)-
• Synonyms: 1H-Benz[de]isoquinolin-1-one,2-(3S)-1-azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-,(3aR)-;Palonosetron Diastereomers(R.S)
• CAS NO: 135729-73-6
• Molecular Formula: C19H24N2O
• Molecular Weight: 296.40666
• Mol File: 135729-73-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 470.4±45.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• PKA: 9.77±0.33(Predicted)
• CAS DataBase Reference: 1H-Benz[de]isoquinolin-1-one,2-(3S)-1-azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-,(3aR)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Benz[de]isoquinolin-1-one,2-(3S)-1-azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-,(3aR)-(135729-73-6)
• EPA Substance Registry System: 1H-Benz[de]isoquinolin-1-one,2-(3S)-1-azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-,(3aR)-(135729-73-6)

Safety Data

• Hazardous Substances Data: 135729-73-6(Hazardous Substances Data)

Usage

General Description

The chemical "1H-Benz[de]isoquinolin-1-one,2-(3S)-1-azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-,(3aR)-" is a complex organic compound with a fused benzene and isoquinoline ring structure. It also contains a 1-azabicyclo[2.2.2]octane fragment. The compound is a hexahydro derivative, meaning it has six saturated carbon atoms in a ring structure. The stereochemistry of the compound is specified by the (3S) and (3aR) designations, indicating the orientation of the substituents on the molecule. 1H-Benz[de]isoquinolin-1-one,2-(3S)-1-azabicyclo[2.2.2]oct-3-yl-2,3,3a,4,5,6-hexahydro-,(3aR)- may have potential pharmacological or biological activity due to its complex structure and the presence of multiple functional groups.

Upstream product

• 135729-55-4 (S)-2-<1-azabicyclo<2.2.2>oct-3-yl>-2,4,5,6-tetrahydro-1-oxo-1H-benzisoquinoline hydrochloride 
• 135729-57-6 2-<(R)-1-azabicyclo<2.2.2>oct-3-yl>-1,2,4,5-tetrahydro-1H-benzisoquinolin-1-one 
• 135729-78-1 N-<(S)-1-azabicyclo<2.2.2>oct-3-yl>-5,6,7,8-tetrahydronaphthalene-1-carboxamide 
• 110808-69-0 5,6,7,8-tetrahydronaphthylene-1-carboxylic acid chloride 
• 4242-18-6 5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid 
• 135729-56-5 (S)-2-(1-azabicyclo[2.2.2]oct-3-yl)-2,4,5,6-tetrahydro-1H-benz[de]isoquinolin-1-one 
• 177793-80-5 C₁₈H₂₆N₂ 
• 85977-52-2 (S)-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid 
• 177793-79-2 N-(1-azabicyclo[2.2.2]oct-3S-yl)-1,2,3,4-tetrahydronaphthalene-1S-carboxamide 
• 135729-55-4 palonosetron hydrochloride 
• 135755-51-0 palonosetron hydrochloride 

Downstream Products

• 135755-51-0 palonosetron hydrochloride 
• 135755-51-0 palonosetron hydrochloride 
• 813425-83-1 Palonosetron N-oxide 

Relevant articles and documents

A hydrochloric acid palonosetron production method

The invention belongs to the field of organic synthesis, and particularly relates to a production method of high-purity and high-yield palonosetron hydrochloride. Chiral compounds, namely, (S)-(-)-1,2,3,4-tetrahedro-naphthoic acid and S-3-aminoquinuclidine, are taken as raw materials, and an intermediate is obtained; the intermediate has a reduction reaction in the presence of NaBH4 and BF3*CH3OH, a product is added to a hydrochloric acid aqueous solution for a reflux reaction after the reaction, and a transparent oily substance is obtained through extraction after the reflux reaction; toluene is added to the substance, a toluene solution of triphosgene is dropwise added again at the temperature ranging from 10 DEG C to 15 DEG C, white solids are separated out, a reaction is performed under the condition of heating reflux, and the toluene solution of the triphosgene is dropwise added again under the reflux condition; then a system is cooled to the temperature ranging from 10 DEG C to 15 DEG C, BF3*CH3OH is added, the system is added to water and the hydrochloric acid aqueous solution at the reflux temperature after addition, then a reflux reaction is performed at the heating reflux temperature, and then a crude product is obtained through washing, extraction and crystallization; the crude product is dissolved in acetone, repeated crystallization is performed after dissolution, and the refined palonosetron hydrochloride is obtained. Steps are simple and convenient, reaction conditions are mild, and the production method is easy to operate and suitable for industrial production.

Process for the Preparation of Substantially Pure Palonosetron and its Acid Salts

This invention relates to an improved and scalable process for the preparation of substantially pure palonosetron and its acid addition salts, in particular hydrochloride (I) which comprises of, (a) converting intermediate (IIa) as such or as its freebase (II) to a crude mixture of diastereomeric palonosetrons (VIII) or (VIIIa) contaminated with varying amounts of unconverted intermediate (II) or (IIa) via hydrogenation under pressure with an appropriately chosen hydrogenation catalyst in an suitable organic solvent.(b) making the resulting crude mixture of diastereomeric palonosetrons (VIII) or (VIIIa) contaminated with varying amounts of unconverted intermediate (II) or (IIa) substantially free from (II) or (IIa) via halogenation reaction.(c) Finally, converting the resulting diastereomeric palonosetron (VIII) or its hydrochloride (VIIIa) substantially free from intermediate (II) or (IIa) to the desired palonosetron hydrochloride (I) in substantially pure form via selective crystallization from a suitable single or mixture of organic solvents.

HIGH PURITY PALONOSETRON BASE AND ITS SOLID STATE CHARACTERISTICS

The present invention describes the process for the preparation of pure enantiomeric form of palonosetron base of formula (I), and its solid-state characteristics of said compound.