76272-56-5

Basic information

• Product Name: Endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane
• Synonyms: 1-AMINO-9-METHYL-9-AZABICYCLO[3,3,1]-NONANE;9-METHYL-9-AZA-BICYCLO[3,3,1]NON-3-YL-AMINE;ENDO-3-AMINE-9-METHYL-9-AZABICYCLO[3,3,1]NONAN;ENDO-3-AMINE-9-METHYL-9-AZABICYCLO[3,3,1]NONANE;ENDO-3-AMINE-9-METHYL-AZABICYCLO[3.3.1] NONANE;ENDO-3-AMINO-9-METHYL-9-AZABICYCLO[3.3.1]NONANE;ENDO-9-METHYL-9-AZA-BICYCLO[3.3.1]NON-3-YLAMINE;ENDO-9-METHYL-9-AZABICYCLO3,3,1-NONAN-3-AMINE
• CAS NO: 76272-56-5
• Molecular Formula: C₉H₁₈N₂
• Molecular Weight: 154.25
• EINECS: 1806241-263-5
• Product Categories: Amines and Anilines;Heterocycles;(intermediate of granisetron);Amines;Chiral Reagents;Impurities;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 76272-56-5.mol

Chemical Properties

• Boiling Point: 115-119°C (18 mmHg)
• Flash Point: 72.1 °C
• Appearance: Pale yellow oil
• Density: 0.968 g/cm³
• Vapor Pressure: 0.545mmHg at 25°C
• Refractive Index: 1.517
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 11.09±0.40(Predicted)
• CAS DataBase Reference: Endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane(CAS DataBase Reference)
• NIST Chemistry Reference: Endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane(76272-56-5)
• EPA Substance Registry System: Endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane(76272-56-5)

Safety Data

• Hazardous Substances Data: 76272-56-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C9H18N2/c1-11-8-4-2-6-9(11,10)7-3-5-8/h8H,2-7,10H2,1H3

Upstream product

• 6164-67-6 9-methyl-9-aza-bicyclo[3.3.1 ]nonan-3-one oxime 
• 111-30-8 Glutaraldehyde 
• 135906-03-5 C₉H₁₈N₂*ClH 
• 552-70-5 pseudopelletierine 

Downstream Products

• 109889-09-0 granisetron 
• 127472-42-8 endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-2-methyl-2H-indazole-3-carboxamide 
• 139632-32-9 1-(2-Methoxy-benzoyl)-3-((1R,3R,5S)-9-methyl-9-aza-bicyclo[3.3.1]non-3-yl)-urea 
• 114559-59-0 endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-N'-(2-methyoxyphenyl)urea 
• 124998-65-8 granisetron 
• 107007-95-4 endo-N-(9-methyl-9-azabicyclo<3.3.1>nonan-3-yl)-1H-indazole-3-carboxamide 
• 107007-99-8 granisetron hydrochloride 
• 1001347-65-4 4-amino-2,5-difluoro-N-[(1S,5R)-9-methyl-9-azabicyclo[3.3.1]non-7-yI]benzamide 
• 1001346-74-2 4-amino-3-fluoro-N-[(1S,5R)-9-methyl-9-azabicyclo[3.3.1]non-7-yI]benzamide 
• 1001346-73-1 4-amino-3-methoxy-N-((1S,5R)-9-methyl-9-azabicyclo[3.3.1]non-7-yl)benzamide 
• 1007168-25-3 C₂₄H₂₈N₄O₃ 
• 1314704-67-0 N-(2-bromophenyl)-9-methyl-9-azabicyclo[3.3.1]nonan-3-amine 

Relevant articles and documents

Preparation method of granisetron intermediate

The invention discloses a preparation method of a granisetron intermediate. The preparation method comprises the following steps: step 1, carrying out a Mannich reaction on acetone dicarboxylic acid represented by a formula III to obtain pseudopelletierine represented by a formula IV; step 2, carrying out a reaction on the pseudopelletierine and hydroxylamine to prepare 3-pseudopelletierine oximerepresented by a formula V; and step 3, carrying out preparation by adopting one of the following schemes: (1) carrying out catalytic reduction on the 3-pseudopelletierine oxime through sodium bis(2-methoxyethoxy)aluminumhydride and Lewis acid to obtain a crude product of endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane represented by a formula I, and directly using the crude product of endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane to prepare granisetron, or purifying the crude product of endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane for preparing granisetron; and (2) carrying out catalytichydrogenation reduction on the 3-pseudopelletierine oxime through Raney nickel to obtain a mixture of endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane, purifying the mixture to obtain endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane represented by the formula I, and using the endo-3-amine-9-methyl-9-azabicyclo[3,3,1]nonane used for preparing granisetron. The method has the advantages of mild reaction conditions, high reaction yield and low cost, and is suitable for industrial production.

Efficient syntheses of exo-granisetron hydrochloride and other potential impurities present in granisetron hydrochloride, an anti-emetic drug

European Pharmacopeia mentions about nine potential impurities in Granisetron hydrochloride. These impurities need to be controlled in the API as described in the Pharmacopeia. Elegant syntheses of four potential impurities in Granisetron hydrochloride are disclosed.

Toward biophysical probes for the 5-HT3 receptor: Structure-activity relationship study of granisetron derivatives

This report describes the synthesis and biological characterization of novel granisetron derivatives that are antagonists of the human serotonin (5-HT3A) receptor. Some of these substituted granisetron derivatives showed low nanomolar binding affinity and allowed the identification of positions on the granisetron core that might be used as attachment points for biophysical tags. A BODIPY fluorophore was appended to one such position and specifically bound to 5-HT3A receptors in mammalian cells.

Process for the production of aminoazobicycloalkanes from oximes

A process for preparing a compound of formula (I), wherein n is 2 or 3; which process comprises reducing a compound of formula (II), wherein R1 is hydrogen or C1-4 alkyl and n is 2 or 3; by catalytic hydrogenation in the presence of a rhodium catalyst. STR1