63971-25-5

Basic information

• Product Name: 3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride
• Synonyms: 3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride;1-Hydroxy-3-amino-5,7-dimethyladamantane;2. 1-Hydroxy-3-amino-5,7-dimethyladamantane;1-Amino-7-hydroxy-3,5-dimethyladamantane;Memantine impurity F
• CAS NO: 63971-25-5
• Molecular Formula: C₁₂H₂₁NO
• Molecular Weight: 195.3
• Product Categories: Adamantane derivatives;Amines;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals
• Mol File: 63971-25-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 269.4 °C at 760 mmHg
• Flash Point: 116.8 °C
• Appearance: /
• Density: 1.197 g/cm³
• Vapor Pressure: 0.000964mmHg at 25°C
• Refractive Index: 1.608
• PKA: 15.11±0.70(Predicted)
• CAS DataBase Reference: 3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride(63971-25-5)
• EPA Substance Registry System: 3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride(63971-25-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 63971-25-5(Hazardous Substances Data)

Usage

General Description

3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride is a chemical compound with the molecular formula C13H22ClNO. It is a derivative of adamantane, a tricyclic hydrocarbon and has a hydrochloride salt form. 3-AMINO-5,7-DIMETHYLADAMANTAN-1-OL Hydrochloride is a white solid with potential applications in pharmaceutical research and development. It has a wide range of pharmacological properties, including antiviral, antitumor, and antiparkinsonian activities, and has been studied for its potential role in the treatment of various neurological disorders. Its unique structure and potential biological activities make it a valuable candidate for further research and potential therapeutic applications.

InChI:InChI=1/C12H21NO/c1-9-3-10(2)5-11(13,4-9)8-12(14,6-9)7-10/h14H,3-8,13H2,1-2H3

Synthetic route

1-acetamido-3,5-dimethyladamantane (19982-07-1) → N-(3-hydroxy-5,7-dimethyladamantan-1-yl)acetamide (351329-87-8) + 1,3-dihydroxy-5,7-dimethyladamantane (10347-01-0) + 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5)

Conditions	Yield
Stage #1: 1-acetamido-3,5-dimethyladamantane With nitric acid Stage #2: With acetic acid; urea In water	A 17% B 9% C n/a

C22H38N2O5 → 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: dichloromethane / 1 h / 20 °C 2: hydrogen / methanol / 12 h View Scheme

C12H22N2O*C2HF3O2 → 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5)

Conditions	Yield
With hydrogen In methanol for 12h;

1,3-dimethyl-5-adamantanol (707-37-9) → 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrabutyl-ammonium chloride; methanol; cerium(III) chloride / acetonitrile / 16 h / 20 °C / Irradiation; Inert atmosphere; Sealed tube 2: dichloromethane / 1 h / 20 °C 3: hydrogen / methanol / 12 h View Scheme

memantine hydrochloride (41100-52-1) → 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5)

Conditions	Yield
With sulfuric acid; nitric acid at 20℃; for 39h; Cooling with ice;	4.4 g

1-acetamido-3,5-dimethyladamantane (19982-07-1) → 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: potassium hydroxide; butan-1-ol / 130 °C 1.2: pH 8 - 9 2.1: sulfuric acid; nitric acid / 39 h / 20 °C / Cooling with ice View Scheme

3,5-dimethyl-1-bromoadamantane (941-37-7) → 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5)

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 8 h / 130 °C 2.1: potassium hydroxide; butan-1-ol / 130 °C 2.2: pH 8 - 9 3.1: sulfuric acid; nitric acid / 39 h / 20 °C / Cooling with ice View Scheme

3-amino-5,7-dimethyladamantan-1-ol (63971-25-5) + 3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanoic acid (89139-48-0) → N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 70h; Inert atmosphere;	36%

3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanoic acid + 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5) → N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-3-(4-fluoro-3-oxobenzo[d]isothiazol-2(3H)-yl)propanamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 70h; Inert atmosphere;	25%

3-amino-5,7-dimethyladamantan-1-ol (63971-25-5) + 2-(3-Oxo-3h-benzo[d]isothiazol-2-yl)-acetic acid (82152-06-5) → N-(3-hydroxy-5,7-dimethyladamantan-1-yl)-2-(3-oxobenzo[d]isothiazol-2(3H)-yl)acetamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 70h; Inert atmosphere;	17%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 70h;	17%

phthalic anhydride (85-44-9) + 3-amino-5,7-dimethyladamantan-1-ol (63971-25-5) → C20H23NO3 (847278-49-3)

Conditions	Yield
at 30 - 100℃;

3-amino-5,7-dimethyladamantan-1-ol (63971-25-5) → 1-hydroxy-3-amino-5,7-dimethyladamantane hydrochloride (356572-08-2)

Conditions	Yield
With hydrogenchloride In ethyl acetate	68.5 mg

3-amino-5,7-dimethyladamantan-1-ol (63971-25-5) → 1-nitro-7-hydroxy-3,5-dimethyladamantane

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In 1,2-dichloro-ethane for 3h; Reflux;	3.8 g

Upstream product

• 941-37-7 3,5-dimethyl-1-bromoadamantane 
• 19982-07-1 1-acetamido-3,5-dimethyladamantane 
• 41100-52-1 memantine hydrochloride 
• 707-37-9 1,3-dimethyl-5-adamantanol 

Downstream Products

• 356572-08-2 1-hydroxy-3-amino-5,7-dimethyladamantane hydrochloride 

Relevant articles and documents

Memantine hydrochloride impurity compound and preparation method thereof

The invention discloses a preparation method of a memantine hydrochloride impurity compound 1-nitro-7-hydroxy-3,5-dimethyl adamantane. According to the preparation method, 1-bromo-3,5-dimethyl adamantane is taken as a raw material and carries out a substitution reaction with acetamide in a molten state, then hydrolysis and salt forming happen in an alkaline environment, and finally the target product is prepared after hydroxylation and oxidation. The impurity compound is used as a reference substance for memantine hydrochloride quality control.

One-pot synthesis of cage alcohols

An efficient one-pot procedure has been developed for the synthesis of cage alcohols with hydroxy groups in the bridgehead positions. The procedure includes initial nitroxylation with nitric acid or a mixture of nitric acid with acetic acid and subsequent hydrolysis in the presence of urea.