2-Aminoadamantane hydrochloride

Base Information

• Chemical Name: 2-Aminoadamantane hydrochloride
• CAS No.: 10523-68-9
• Molecular Formula: C10H17N.HCl
• Molecular Weight: 187.713
• Hs Code.: 29213000
• European Community (EC) Number: 234-074-2
• DSSTox Substance ID: DTXSID60147021
• ChEMBL ID: CHEMBL447911
• Mol file: 10523-68-9.mol

Synonyms:2-aminoadamantane;2-aminoadamantane hydrochloride;2-aminoadamantane sulfate (1:1);2-aminoadamantane sulfate (2:1)

Chemical Property of 2-Aminoadamantane hydrochloride

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 0.0831mmHg at 25°C
• Melting Point: >300 °C(lit.)
• Boiling Point: 226.1 °C at 760 mmHg
• Flash Point: 96.5 °C
• PSA: 26.02000
• LogP: 3.27210
• Storage Temp.: Inert atmosphere,Room Temperature
• Solubility.: DMSO (Slightly), Methanol (Slightly), Water (Slightly)
• Water Solubility.: soluble
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 187.1127773
• Heavy Atom Count: 12
• Complexity: 148

Purity/Quality:

≥99.0% ^*data from raw suppliers

2-Adamantanamine Hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-36/37/39-22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C2CC3CC1CC(C2)C3N.Cl
• Uses: 2-Adamantylamine hydrochloride was used to prepare 2-adamantylamide of 2?-(carboxymethoxime)-olivomycin I. The HPLC assay of 2-adamantylamine hydrochloride after pre-column derivatization with 4-fluoro-7-nitro-2,1,3-benzoxadiazole has been studied. It is also used as an important raw material and intermediate used in organic Synthesis, pharmaceuticals, agrochemicals and dyestuff. 2-Adamantanamine Hydrochloride can be used to prepare CD73 inhibitors to treat CD73-associated diseases, including cancer and immune-related disorders.

Technology Process of 2-Aminoadamantane hydrochloride

There total 3 articles about 2-Aminoadamantane hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

2-adamantanone oxime (4500-12-3) → 1-adamantanol (700-57-2) + adamantan-2-amine hydrochloride (10523-68-9)

Guidance literature:

2-adamantanone oxime; With NiAl₂; potassium hydroxide; In tetrahydrofuran; water; Reflux;

With hydrogenchloride; In tetrahydrofuran; tert-butyl methyl ether;

DOI:10.1134/S1070428019110162

Reference yield:

2-Adamantanone (700-58-3) → 1-adamantanol (700-57-2) + adamantan-2-amine hydrochloride (10523-68-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 20 °C

2: potassium hydroxide; NiAl₂ / water; tetrahydrofuran / Reflux

With hydroxylamine hydrochloride; NiAl₂; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; ethanol; water;

DOI:10.1134/S1070428019110162

Reference yield:

adamantane (281-23-2) → amantadine hydrochloride (665-66-7,13878-11-0) + adamantan-2-amine hydrochloride (10523-68-9)

Guidance literature:

adamantane; With methanol; cerium(III) chloride; di-tert-butyl-diazodicarboxylate; tetrabutyl-ammonium chloride; In acetonitrile; at 20 ℃; for 10h; Irradiation; Inert atmosphere; Sealed tube;

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h; Reagent/catalyst; Further stages;

DOI:10.1021/jacs.0c00212

upstream raw materials:

2-Adamantanone

2-adamantanone oxime

adamantane

Downstream raw materials:

2-(5-bromonicotinoylamino)adamantane

N-(2-Adamantyl)2-oxo-4-phenylpyrrolidine-1-acetamide

4-aminoadamantan-1-ol

2-(adamantan-2-ylcarbarmoyl)-piperidine-1-carboxylic acid benzyl ester

Refernces

• 1、 Brunilin, R. V.,Mkrtchyan, A. S.,Nawrozkij, M. B.,Novakov, I. A.,Vernigora, A. A.,Voloboev, S. N.,Vostrikova, O. V.. "Potential Synthetic Adaptogens: V. Synthesis of Cage Monoamines by the Schwenk–Papa Reaction". . p. 1742 - 1748. Retrieved 2020/01/11.