1-Acetamidoadamantane

Base Information

• Chemical Name: 1-Acetamidoadamantane
• CAS No.: 880-52-4
• Molecular Formula: C12H19NO
• Molecular Weight: 193.289
• Hs Code.: 29242998
• European Community (EC) Number: 212-914-9
• NSC Number: 527917
• UNII: 5283Y1VOII
• DSSTox Substance ID: DTXSID9061255
• Nikkaji Number: J286K
• Wikidata: Q27260972
• Mol file: 880-52-4.mol

Synonyms:1-Acetamidoadamantane;880-52-4;N-(1-Adamantyl)acetamide;N-(adamantan-1-yl)acetamide;1-Acetylaminoadamantane;n-adamantylacetamide;1-Adamantylacetamide;N-1-Adamantylacetamide;Acetamide, N-1-adamantyl-;N-Acetyl Adamantamine;EINECS 212-914-9;Acetamide, N-tricyclo(3.3.1.13,7)dec-1-yl-;Acetamide, N-tricyclo[3.3.1.13,7]dec-1-yl-;NSC 527917;BRN 2098306;UNII-5283Y1VOII;5283Y1VOII;Acetamide, N-(1-adamantyl)-;NSC-527917;N-[1-Adamantyl]acetamide;N-Tricyclo(3.3.1.13,7)dec-1-ylacetamide;4-12-00-00220 (Beilstein Handbook Reference);N-tricyclo[3.3.1.13,7]dec-1-ylacetamide;1-Acetamino adamantane;Acetamide, N-tricyclo(3.3.1.1(3,7)-)dec-1-yl-;Acetamide, N-tricyclo[3.3.1.1(3,7)-]dec-1-yl-;1-Acetamidotricyclo[3.3.1.1(3,7)]decane;MFCD00074730;NSC527917;Acetamide,7]dec-1-yl-;N-Acetyl-1-adamantanamine;N-ACETYL AMANTADINE;SCHEMBL133014;DTXSID9061255;SCHEMBL14283216;SCHEMBL19757636;AMY22323;STK355738;AKOS000472072;AKOS001064174;AB02845;CS-O-30529;LS-8000;NCGC00322546-01;AC-16090;A0737;CS-0159104;FT-0629068;Acetamide, N-tricyclo[3.3.1.1]dec-1-yl-;F15406;AB00694312-03;EN300-8601068;A842454;N-(tricyclo[3.3.1.1~3,7~]dec-1-yl)acetamide;acetamide, N-tricyclo[3.3.1.1~3,7~]dec-1-yl-;W-100421;W-200099;Q27260972;Z27687036;AMANTADINE HYDROCHLORIDE IMPURITY B [EP IMPURITY];N-(TRICYCLO(3.3.1.13,7)DEC-1-YL)ACETAMIDE

Chemical Property of 1-Acetamidoadamantane

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 3.45E-05mmHg at 25°C
• Melting Point: 148-149 °C (lit.)
• Refractive Index: 1.533
• Boiling Point: 354 °C at 760 mmHg
• PKA: 16.16±0.20(Predicted)
• Flash Point: 210.6 °C
• PSA: 29.10000
• Density: 1.08 g/cm³
• LogP: 2.48220
• Storage Temp.: 0-6°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 193.146664230
• Heavy Atom Count: 14
• Complexity: 230

Purity/Quality:

99% ^*data from raw suppliers

N-AcetylAdamantamine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36-24/25-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)NC12CC3CC(C1)CC(C3)C2
• Uses: A metabolite of Adamantamine

Technology Process of 1-Acetamidoadamantane

There total 85 articles about 1-Acetamidoadamantane 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: 100.0%

Trimethyl orthoacetate (1445-45-0) + amantadine hydrochloride (665-66-7,13878-11-0) → N-(1-adamantyl)acetamide (880-52-4)

Guidance literature:

In methanol; at 135 ℃; for 0.25h; Microwave irradiation;

DOI:10.1080/00397911.2015.1096943

Reference yield: 99.0%

1-adamanthanol (768-95-6) + acetonitrile (75-05-8,26809-02-9) → N-(1-adamantyl)acetamide (880-52-4)

Guidance literature:

With copper(ll) bromide; at 150 ℃; for 8h; Reagent/catalyst; Inert atmosphere; Sealed tube;

DOI:10.1134/S1070428018080031

Reference yield: 97.0%

adamantane (281-23-2) + acetonitrile (75-05-8,26809-02-9) → N-(1-adamantyl)acetamide (880-52-4)

Guidance literature:

With nitrosonium tetrafluoroborate; for 4h; reflux;

DOI:10.1021/jo01289a034

upstream raw materials:

1-adamanthanol

acetonitrile

1-Adamantyl bromide

1-chloroadamantane

Downstream raw materials:

1,3-adamantandiol

3-aminoadamantan-1-ol

N-(3-hydroxyadamantan-1-yl)acetamide

1-adamanthanol

Refernces

• 1、 Novikovskii,Gunchenko,Prikhodchenko,Serguchev,Schreiner,Fokin. "Comparative theoretical and experimental analysis of hydrocarbon σ-radical cations". . p. 1293 - 1299. Retrieved 2011.
• 2、 Kreutzberger,Schroeders. "Amantadine (1 aminoadamantane) as a nucleophilic component in substitution, addition and ring cleavage reactions". . p. 1073 - 1074. Retrieved 1976.
• 3、 Narobe, Rok,Murugesan, Kathiravan,Schmid, Simon,K?nig, Burkhard. "Decarboxylative Ritter-Type Amination by Cooperative Iodine (I/III)─Boron Lewis Acid Catalysis". . p. 809 - 817. Retrieved 2022/01/15.
• 4、 -. "Method for preparing 3-acetamido-1-adamantanol". Paragraph 0026; 0030; 0034. . Retrieved 2021/01/29.