3'-(ethyl(Methyl)carbaMoyl)oxyacetophenone Chemical Properties

Boiling point:

337℃

Density 

1.112

Flash point:

158℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Chloroform (Slightly)

form 

Oil

pka

-1.56±0.70(Predicted)

color 

Colourless

Safety Information

HS Code 

2924296000

3'-(ethyl(Methyl)carbaMoyl)oxyacetophenone Usage And Synthesis

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

3'-(ethyl(Methyl)carbaMoyl)oxyacetophenone(855300-09-3)Related Product Information

• Rivastigmine USP RC E
• 1-(3-Methoxyphenyl)-N,N-diMethylethanaMine
• 3-vinylphenyl ethyl(Methyl)-carbaMate
• (S)-1-(3-((ethyl(methyl)carbamoyl)oxy)phenyl)-N,N-dimethylethanamine
• S-(-)-[1-(3-Methoxyphenyl)ethyl]-N,N-diMethylaMine
• 1-(3-METHOXY-PHENYL)-ETHANOL
• Rivastigmine tartrate
• 3-Methoxyacetophenone
• 3-[(1S)-1-(Dimethylaminoethyl)]phenol
• Rivastigmine N-Oxide
• Rivastigmine Impurity 9
• (R,S)-3-[1-(Dimethylamino)ethyl]phenyl dimethylcarbamate
• 1-chloro-1-(3'-methoxyphenyl)ethane
• (αS)-N,N,α-TriMethyl-3-(4-nitrophenoxy)benzeneMethanaMine
• Rivastigmine EP Impurity E
• Diethyl RivastigMine