| Identification | Back Directory | [Name]
1-AMINO-3-ADAMANTANECARBOXYLIC ACID HYDROCHLORIDE | [CAS]
6240-01-3 | [Synonyms]
IFLAB-BB F0035-0250
3-AMino-1-CarboxyadaMantane Hydrochloride
3-Amino-1-adamantanecarboxylate hydrochloride
3-Amino-1-adamantanecarboxylic acid hydrochloride
3-AMINOADAMANTANE-1-CARBOXYLIC ACID HYDROCHLORIDE
1-AMINO-3-ADAMANTANECARBOXYLIC ACID HYDROCHLORIDE
3-Aminotricyclo[3.3.1.13,7]decane-1-carboxylic acid hydrochloride
3-Aminoadamantane-1-carboxylic acid-4-ethylbenzenesulfonic acid (1:1) | [Molecular Formula]
C11H18ClNO2 | [MDL Number]
MFCD01825827 | [MOL File]
6240-01-3.mol | [Molecular Weight]
231.72 |
| Chemical Properties | Back Directory | [Melting point ]
>300℃ (DEC.) | [storage temp. ]
Inert atmosphere,Room Temperature | [Appearance]
White to off-white Solid | [InChI]
InChI=1/C11H17NO2.ClH/c12-11-4-7-1-8(5-11)3-10(2-7,6-11)9(13)14;/h7-8H,1-6,12H2,(H,13,14);1H/t7-,8+,10+,11-; | [InChIKey]
CMUAQGBJDDHTPE-GVRPCFNPNA-N | [SMILES]
[C@]12(C(=O)O)C[C@@]3([H])C[C@]([H])(C[C@](N)(C3)C1)C2.Cl |&1:0,5,8,11,r| |
| Hazard Information | Back Directory | [Uses]
3-Aminoadamantane-1-carboxylic acid hydrochloride is an amino acid hydrochloride containing an adamantane skeleton, which can be prepared by the hydrochloric acid hydrolysis of 3-acetamidoadamantane carboxylic acid. Its primary use is as a synthetic intermediate, particularly for the preparation of N-Boc-aminoadamantane carboxylic acid following Boc protection, which is then used to synthesize neuropharmacologically active molecules such as P2X7-NMDA dual receptor antagonists. It can also be used to synthesize N-acyl-aminoadamantane derivatives via benzylation[1-2]. | [Synthesis]
3-Aminoadamantane-1-carboxylic acid hydrochloride is prepared from adamantane-1-carboxylic acid as the starting material through a two-step reaction [1].
Step 1: Adamantane-1-carboxylic acid undergoes a Ritter reaction with acetonitrile in an electrophilic medium (98% H₂SO₄, 54% HNO₃, 20% fuming sulfuric acid) to synthesize 3-acetamido-1-adamantane carboxylic acid with a yield of 78.7%. High-purity 3-acetylamino-1-adamantane carboxylic acid can also be obtained by reacting 3-hydroxy-1-adamantane carboxylic acid with acetonitrile in a sulfuric acid medium.
Step 2: 3-Acetylamino-1-adamantane carboxylic acid is subjected to acid hydrolysis by boiling in an aqueous hydrochloric acid solution for 5–10 hours. Hydrolysis yields the main product, 3-amino-1-adamantane carboxylic acid hydrochloride, and the byproduct, 3-chloroadamantane-1-carboxylic acid; treating the mixture with acetone yields a pure hydrochloride product (Compound 3).
 | [References]
[1] Zurabishvili, D. Lomidze, M. Gogolashvili, I. Trapaidze, M. Samsoniya, S. Kazmaier, Uli. (2017). Synthesis of derivatives of acylaminoadamantane carboxylic acids and some transformations. Bulletin of the Georgian National Academy of Sciences. 11. 61-66.
[2] Olga Karoutzou. (2018). Towards a Novel Class of Multitarget-Directed Ligands: Dual P2X7-NMDA Receptor Antagonists. Molecules. https://doi.org/10.3390/molecules23010230
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| Company Name: |
Energy Chemical
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| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Cool Pharm, Ltd
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| Telephone: |
021-60455363 18019463053 |
| Website: |
www.coolpharm.com |
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