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19982-07-1

19982-07-1 Structure

19982-07-1 Structure
IdentificationMore
[Name]

1-Actamido-3,5-dimethyladmantane
[CAS]

19982-07-1
[Synonyms]

1-actamido-3,5-dimethyladmantane
n-(3,5-dimethyl-1-adamantyl)-acetamide
1-ACETAMIDO-3,5-DIMETHYLADMANTANE
1-Acetamido-3,5-dimethyladamantane
1-acetate amino-3,5-Dimethyl Adamantane
1. 1-actamido-3,5-dimethyladmantane
[EINECS(EC#)]

606-412-2
[Molecular Formula]

C14H23NO
[MDL Number]

MFCD06656139
[Molecular Weight]

221.339
[MOL File]

19982-07-1.mol
Chemical PropertiesBack Directory
[Melting point ]

110-111°C
[Boiling point ]

348.5±9.0 °C(Predicted)
[density ]

1.05
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

Chloroform (Sparingly), Ethyl Acetate (Slightly)
[form ]

Solid
[pka]

16.20±0.60(Predicted)
[color ]

White
[CAS DataBase Reference]

19982-07-1(CAS DataBase Reference)
Safety DataBack Directory
[Symbol(GHS) ]

Flame Over Circle (GHS03)Exclamation Mark (GHS07)
GHS03,GHS07
[Signal word ]

Warning
[Hazard statements ]

H227
[Precautionary statements ]

P501-P210-P280-P370+P378-P403+P235
[HS Code ]

2902190000
Hazard InformationBack Directory
[Chemical Properties]

1-Actamido-3,5-dimethyladmantane is White Solid
[Uses]

1-Actamido-3,5-dimethyladmantane is an intermediate used for preparation of Memantine (M218000).
[Synthesis]

3,5-Dimethyl-1-adamantanol

707-37-9

Acetonitrile

75-05-8

1-Actamido-3,5-dimethyladmantane

19982-07-1

[0063] 1.00 g (5.50 mmol) of 3,5-dimethyl-1-adamantanol, 0.46 g (11.1 mmol) of acetonitrile, and 9.61 g of homotrimethylbenzene were added to a test tube with an outer diameter of 30 mm and mixed well. Subsequently, 1.12 g (11.1 mmol) of 97% concentrated sulfuric acid was slowly added dropwise to the mixed solution in the test tube to form a reaction solution. The reaction solution was stirred at a constant temperature at 30°C for 3 hours to promote the reaction. Upon completion of the reaction, 6.09 g of water was added to the reaction solution to quench the reaction, and the aqueous phase was removed by aqueous washing to obtain a homotrimethylbenzene solution containing 1-acetamido-3,5-dimethyladamantane (reaction yield: 80.4%). Next, 0.71 g of sodium hydroxide hydrate and 9.61 g of 1-hexanol were added to this solution to prepare a reaction solution. The reaction solution was stirred at 130 °C for 18 h to achieve hydrolysis of 1-acetamido-3,5-dimethyladamantane. Finally, the reaction solution was analyzed by gas chromatography (GC) to confirm the generation of memantine (reaction yield: 96.2%).

[References]

[1] Journal of Organic Chemistry USSR (English Translation), 1982, vol. 18, p. 867 - 871
[2] Zhurnal Organicheskoi Khimii, 1982, vol. 18, # 5, p. 1001 - 1005
[3] Patent: EP2949643, 2015, A1. Location in patent: Paragraph 0063
Spectrum DetailBack Directory
[Spectrum Detail]

1-Actamido-3,5-dimethyladmantane(19982-07-1)1HNMR
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