101353-61-1

Basic information

• Product Name: endo-N-Benzyl-endo-3-aminotropane
• Synonyms: endo-N-Benzyl-endo-3-aminotropane;endo-N-Benzyl-8-Methyl-8-azabicyclo[3.2.1]octan-3-aMine;8-Azabicyclo[3.2.1]octan-3-amine,8-methyl-N-(phenylmethyl)-;Tropane,3-benzylamino- (6CI)
• CAS NO: 101353-61-1
• Molecular Formula: C₁₅H₂₂N₂
• Molecular Weight: 230.35
• EINECS: 1533716-785-6
• Product Categories: Heterocycle
• Mol File: 101353-61-1.mol

Chemical Properties

• Boiling Point: 334.488 °C at 760 mmHg
• Flash Point: 129.32 °C
• Appearance: /
• Density: 1.065 g/cm³
• Vapor Pressure: 0.000127mmHg at 25°C
• Refractive Index: 1.578
• CAS DataBase Reference: endo-N-Benzyl-endo-3-aminotropane(CAS DataBase Reference)
• NIST Chemistry Reference: endo-N-Benzyl-endo-3-aminotropane(101353-61-1)
• EPA Substance Registry System: endo-N-Benzyl-endo-3-aminotropane(101353-61-1)

Safety Data

• Hazardous Substances Data: 101353-61-1(Hazardous Substances Data)

Usage

Uses

Used in Neurological Disorders Treatment:
Endo-N-Benzyl-endo-3-aminotropane is used as a therapeutic agent for the treatment of Parkinson's disease and other movement disorders. It functions by inhibiting dopamine reuptake and blocking acetylcholine action, leading to enhanced motor control and reduced symptoms of tremors and rigidity.
Used in Adjunct Treatment for Drug-Induced Extrapyramidal Symptoms:
Endo-N-Benzyl-endo-3-aminotropane is utilized as an adjunct treatment for drug-induced extrapyramidal symptoms, helping to manage and alleviate the side effects associated with certain medications.
Used in Cocaine Addiction Research:
Endo-N-Benzyl-endo-3-aminotropane has been investigated for its potential in treating cocaine addiction, suggesting its possible use in addiction medicine to help individuals overcome substance abuse.
Available in Oral and Injectable Forms:
Endo-N-Benzyl-endo-3-aminotropane is available in both oral and injectable forms, providing flexibility in administration and catering to different patient needs and preferences.
Tolerability and Side Effects:
Endo-N-Benzyl-endo-3-aminotropane is generally well-tolerated by individuals, but it may cause side effects such as dry mouth, dizziness, and constipation in some cases.

InChI:InChI=1/C15H22N2/c1-17-14-7-8-15(17)10-13(9-14)16-11-12-5-3-2-4-6-12/h2-6,13-16H,7-11H2,1H3

Upstream product

• 35130-97-3 (1R,3R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl-methane sulfonate 
• 100-46-9 benzylamine 
• 532-24-1 tropinone 
• 13514-03-9 3-chlorotropan 
• 120-29-6 3-tropanol 
• 135-97-7 pseudotropine 
• 532-24-1 tropinone 

Downstream Products

• 110176-96-0 benzyl-methyl-tropane-3endo-yl-amine 
• 716353-96-7 C₃₅H₃₇N₃O₃ 

Relevant articles and documents

A modified palladium catalysed reductive amination procedure

New, extended applications of a modified palladium catalysed reductive amination procedure are described; a mechanistic hypothesis alternative to the common imine pathway is proposed. This versatile method advances the usual reductive amination processes

Novel 4,4-disubstituted piperidine-based C-C chemokine receptor-5 inhibitors with high potency against human immunodeficiency virus-1 and an improved human ether-a-go-go related gene (hERG) profile

We recently described (J. Med. Chem. 2008, 51, 6538-6546) a novel class of CCR5 antagonists with strong anti-HIV potency. Herein, we detail SAR converting leads 1 and 2 to druglike molecules. The pivotal structural motif enabling this transition was the secondary sulfonamide substituent. Further finetuning of the substituent pattern in the sulfonamide paved the way to enhancing potency and bioavailability and minimizing hERG inhibition, resulting in discovery of clinical compound 122 (GSK163929).

Hydride reagents for stereoselective reductive amination. An improved preparation of 3-endo-tropanamine

The reductive amination of substituted cyclohexanones with sodium triacyloxyborohydrides derived from NaBH4 and various carboxylic acids provides highly diastereoselective conversions to protected axial amines. This method was applied to the stereoselective preparation of 3-endo-tropanamine.

Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures

Sodium triacetoxyborohydride is presented as a general reducing agent for the reductive amination of aldehydes and ketones. Procedures for using this mild and selective reagent have been developed for a wide variety of substrates. The scope of the reaction includes aliphatic acyclic and cyclic ketones, aliphatic and aromatic aldehydes, and primary and secondary amines including a variety of weakly basic and nonbasic amines. Limitations include reactions with aromatic and unsaturated ketones and some sterically hindered ketones and amines. 1,2-Dichloroethane (DCE) is the preferred reaction solvent, but reactions can also be carried out in tetrahydrofuran (THF) and occasionally in acetonitrile. Acetic acid may be used as catalyst with ketone reactions, but it is generally not needed with aldehydes. The procedure is carried out effectively in the presence of acid sensitive functional groups such as acetals and ketals; it can also be carried out in the presence of reducible functional groups such as C-C multiple bonds and cyano and nitro groups. Reactions are generally faster in DCE than in THF, and in both solvents, reactions are faster in the presence of AcOH. In comparison with other reductive amination procedures such as NaBH3CN/MeOH, borane-pyridine, and catalytic hydrogenation, NaBH(OAc)3 gave consistently higher yields and fewer side products. In the reductive amination of some aldehydes with primary amines where dialkylation is a problem we adopted a stepwise procedure involving imine formation in MeOH followed by reduction with NaBH4.