778-09-6

Basic information

• Product Name: N-Acetyl DeMethyl MeMantine
• Synonyms: N-Acetyl DeMethyl MeMantine;1-AcetaMido-3-MethyladaMantane;1-Methyl-3-acetaMidoadaMantane;N-(3-Methyl-1-adaMantyl)acetaMide;N-(3-Methyltricyclo[3.3.1.13,7]dec-1-yl)acetaMide;NSC 179381;1-AcetylaMino-3-Methyl AdaMantane
• CAS NO: 778-09-6
• Molecular Formula: C₁₃H₂₁NO
• Molecular Weight: 207.31194
• Product Categories: Amines;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 778-09-6.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 349.9°Cat760mmHg
• Flash Point: 209.5°C
• Appearance: /
• Density: 1.06g/cm³
• Vapor Pressure: 4.57E-05mmHg at 25°C
• Refractive Index: 1.529
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-Acetyl DeMethyl MeMantine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl DeMethyl MeMantine(778-09-6)
• EPA Substance Registry System: N-Acetyl DeMethyl MeMantine(778-09-6)

Safety Data

• Hazardous Substances Data: 778-09-6(Hazardous Substances Data)

Usage

Uses

An analogue of Adamantane.

InChI:InChI=1/C13H21NO/c1-9(15)14-13-6-10-3-11(7-13)5-12(2,4-10)8-13/h10-11H,3-8H2,1-2H3,(H,14,15)

Synthetic route

1-bromo-3-methyladamantane (702-77-2) + acetonitrile (75-05-8) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
With sulfuric acid at 20℃; for 12h; Ritter Amidation;	90%
With sulfuric acid
Stage #1: 1-bromo-3-methyladamantane; acetonitrile With phosphoric acid at 20 - 87℃; for 18.5h; Stage #2: With sodium hydroxide; water; butan-1-ol In toluene at 20 - 45℃; pH=6 - 7;

1-methyl-adamantane (768-91-2) + acetonitrile (75-05-8) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
Stage #1: 1-methyl-adamantane With sulfuric acid; nitric acid at 0℃; for 6h; Stage #2: acetonitrile at 0℃; for 6h; Ritter-type reaction; Further stages.;	41.6%
(anodic oxidation);

acetamide (60-35-5) + 1-methyl-adamantane (768-91-2) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
With nitric acid at 120℃; for 2h;	70%

3,7-dimethylenebicyclo[3.3.1]nonane (770-14-9) + acetylium tetrafluoroborate (2261-02-1) + acetonitrile (75-05-8) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6) + 1-acetonyl-3-acetylaminoadamantane (118647-96-4)

Conditions	Yield
In dichloromethane at -40℃; for 0.25h;	A 15% B 75%

3-methyl-1-adamantanol (702-81-8) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 85 percent / Ph3P, Br2 / acetonitrile / 30 h / Heating 2: 78 percent / Heating View Scheme

acetamide (60-35-5) + 1-bromo-3-methyladamantane (702-77-2) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
Heating;	78%

3-methyl-1-adamantanol nitrate (101974-65-6) + acetonitrile (75-05-8) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
With sulfuric acid for 3h;	75.8%

1-methyl-adamantane (768-91-2) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: Br2 2: H2SO4 View Scheme
Multi-step reaction with 2 steps 1: bromine / 20 °C / Reflux 2: sulfuric acid / 12 h / 20 °C View Scheme

3,7-dimethylenebicyclo[3.3.1]nonane (770-14-9) + acetonitrile (75-05-8) → 1-acetamido-3-methyltricyclo[3.3.1.13,7]decane (778-09-6)

Conditions	Yield
With sulfuric acid

Upstream product

• 768-91-2 1-methyl-adamantane 
• 75-05-8 acetonitrile 
• 60-35-5 acetamide 
• 702-77-2 1-bromo-3-methyladamantane 
• 770-14-9 3,7-dimethylenebicyclo[3.3.1]nonane 
• 702-81-8 3-methyl-1-adamantanol 
• 101974-65-6 3-methyl-1-adamantanol nitrate 
• 2261-02-1 acetylium tetrafluoroborate 

Downstream Products

• 78056-28-7 3-methyl-1-aminoadamantane 
• 99998-84-2 N'--N-<3-methyl-adamantyl>-harnstoff 

Relevant articles and documents

Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases

A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized. These compounds combined the memantine skeleton and a nitrate moiety, and thus inhibited the N-methyl-d-aspartic acid receptor and released NO in the central nervous system. The biological evaluation results revealed that the new memantine nitrates were effective in protecting neurons against glutamate-induced injury in vitro. Moreover, memantine nitrates dilated aortic rings against phenylephrine-induced contraction. The structure-activity relationships of neuroprotection and vasodilation were both analyzed. In further studies, compound MN-05 significantly protected cortical neurons by inhibiting Ca2+ influx, reducing free radical production and maintaining the mitochondrial membrane potential. Further research on MN-05 is warranted.

PROCESS FOR PREPARING MEMANTINE HYDROCHLORIDE SUBSTANTIALLY FREE OF IMPURITIES

The present invention encompasses processes for preparing Memantine hydrochloride and its derivatives, substantially free of impurities.

SYNTHESIS OF ALKOXYCARBONYLAMINOADAMANTANES AND ACETYLAMINOADAMANTANES IN NITRIC ACID

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