Identification | Back Directory | [Name]
3'-(ethyl(Methyl)carbaMoyl)oxyacetophenone | [CAS]
855300-09-3 | [Synonyms]
RivastigMine USP RC D Rivastigmine EP Imp C Rivastigmine EP Impurity C Rivastigmine USP Impurity D Rivastigmine Impurity C(EP) RivastigMine Related CoMpound D Rivastigmine USP Related Compound D 3-Acetylphenyl ethyl(Methyl)-carbaMate Rivastigmine Hydrogen Tartrate Impurity C (3-acetylphenyl) N-ethyl-N-methylcarbamate 3'-(ethyl(Methyl)carbaMoyl)oxyacetophenone Rivastigmine Hydrogen Tartrate EP Impurity C Ethylmethylcarbamic Acid 3-Acetylphenyl Ester CarbaMic acid, ethylMethyl-, 3-acetylphenyl ester N-Ethyl-N-methylcarbamic acid 3-acetylphenyl ester Rivastigmine Impurity 3(Rivastigmine EP Impurity C) Des [3-(1-DiMethylaMino)ethyl] 3-Acetyl RivastigMine Carbamic acid, N-ethyl-N-methyl-, 3-acetylphenyl ester Rivastigmine EP Impurity C/ Rivastigmine Related Compound D Rivastigmine Related Compound D (3-Acetylphenyl ethyl(methyl)carbamate) (1604825) | [Molecular Formula]
C12H15NO3 | [MDL Number]
MFCD20257239 | [MOL File]
855300-09-3.mol | [Molecular Weight]
221.25 |
Chemical Properties | Back Directory | [Boiling point ]
337℃ | [density ]
1.112 | [Fp ]
158℃ | [storage temp. ]
Inert atmosphere,Room Temperature | [solubility ]
DMSO (Slightly), Chloroform (Slightly) | [form ]
Oil | [pka]
-1.56±0.70(Predicted) | [color ]
Colourless |
Hazard Information | Back Directory | [Uses]
Des [3-(1-dimethylamino)ethyl] 3-acetyl Rivastigmine (Rivastigmine EP Impurity C) is a derivative of Rivastigmine (Tartrate: R541000), and acetylcholinesterase inhibitor that is commonly used to treat dementia associated with Parkinson’s disease and Alzheimer’s disease. | [Synthesis]
Synthesis of 3-O-((N-ethyl, methyl) carbamoyl) acetophenone (7):Acetone (1000 ml) was added to a flask equipped with a reflux condenser and mechanical stirrer. 3'-Hydroxyacetophenone (G) (125 g, 0.919 mol) was added with stirring at room temperature to give a yellow transparent solution. Potassium carbonate (381 g, 2.757 mol, 3 eq.) and N-methyl-N-ethylcarbamoyl chloride (EMCC, 167.5 g, 1.379 mol, 1.5 eq.) were then added all at once. The addition funnel was rinsed with acetone (250 ml) and added to the reaction mixture. The reaction mixture was heated to reflux (55 °C). after 4 h, potassium carbonate (25.5 g, 0.18 mol, 0.2 eq.) and acetone (92 ml, 0.74 v/v) were added in a single addition. after 1 h, potassium carbonate (12.75 g, 0.09 mol, 0.1 eq.) was added in another single addition. Upon completion of the reaction, the reaction material was cooled to about 35°C and filtered under vacuum through a sintered funnel. The solids were discarded and the mother liquor was concentrated to give the crude product (7) as a red liquid. Yield:229 g, yield 112.74%.HPLC purity:96.71%. Sulfated ash:0.4%.1H NMR (δ ppm): 1.41-1.56 (2×t, 3H, N-CH2CH3), 2.6 (s, 3H, COCH3), 3.00 and 3.09 (2×s, 3H, N-CH3), 3.38-3.53 (2×q, 2H, N-CH2CH3), 7.32 (d, 1H, Ar- H), 7.46 (t, 1H, Ar-H), 7.69 (s, 1H, Ar-H), 7.78 (d, 1H, Ar-H). | [References]
[1] Patent: WO2005/61446, 2005, A2. Location in patent: Page/Page column 13-14 [2] Molecules, 2018, vol. 23, # 9, [3] Asian Journal of Chemistry, 2013, vol. 25, # 6, p. 3499 - 3500 [4] Journal of Molecular Catalysis B: Enzymatic, 2013, vol. 91, p. 87 - 92 [5] Tetrahedron Asymmetry, 2013, vol. 24, # 7, p. 374 - 379 |
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