120014-06-4Relevant articles and documents
Industrially scalable synthesis of anti-alzheimer drug donepezil
Gaonkar, Santosh L.,Nadaf,Bilehal, Dinesh,Shetty, Nitinkumar S.
, p. 1999 - 2004 (2017)
This paper describes a simple, efficient and industrially scalable total synthesis of donepezil hydrochloride. The article also reported the X-ray studies of the 2-(1-benzylpiperidin-4-ylmethyliden)-5,6-dimethoxyindan-1-one, an intermediate in the synthesis of donepezil. The crystal structure analysis of 2-(1-benzylpiperidin-4-ylmethyliden)-5,6-dimethoxyindan-1-one shows that it crystallizes in monoclinic class under the space group P121/c1 with cell parameters, a = 17.2992(7) ?, b = 10.1999(4) ?, c = 11.9539(5) ?, β = 103.450(2)°, V = 2051.42(15) ?3 and Z = 4.
New synthesis of donepezil through palladium-catalyzed hydrogenation approach
Elati, Chandrashekar R.,Kolla, Naveenkumar,Chalamala, Subrahmanyeswara Rao,Vankawala, Pravinchandra J.,Sundaram, Venkataraman,Vurimidi, Himabindu,Mathad, Vijayavitthal T.
, p. 169 - 174 (2006)
A new, economical, and efficient process has been developed for large-scale synthesis of donepezil 1, an anti-Alzheimer's drug. The process involves palladium-catalyzed hydrogenation of (2E)-5,6-dimethoxy-2-(pyridin-4- ylmethylene)indan-1-one 6 to provide 5,6-dimethoxy-2-(piperidin-4-ylmethyl) indan-1-one 8 as a key step. Copyright Taylor & Francis LLC.
A metal-free method for the facile synthesis of indanonesviathe intramolecular hydroacylation of 2-vinylbenzaldehyde
He, Guoxue,Ma, Jinyu,Zhou, Jianhui,Li, Chunpu,Liu, Hong,Zhou, Yu
supporting information, p. 1036 - 1040 (2021/02/09)
A facile method for the synthesis of indanones was developed under metal- and additive-free conditions, whereinl-proline served as an efficient and environmentally benign catalyst. Compared with previously synthesized indanones, synthesis by the transition-metal-catalyzed intramolecular hydroacylation of 2-vinylbenzaldehyde provided a more green synthetic pathway to indanone scaffolds with good to excellent yields. More importantly, it could be used to synthsize the anti-AD drug donepezil.
Can Heteroarenes/Arenes Be Hydrogenated Over Catalytic Pd/C Under Ambient Conditions?
Tanaka, Nao,Usuki, Toyonobu
, p. 5514 - 5522 (2020/07/24)
Hydrogenation of over a dozen aromatic compounds, including both heteroarenes and arenes, over palladium on carbon (Pd/C, 1–100 molpercent) with H2-balloon pressure at room temperature is reported. Analyses using pyridine as a model substrate revealed that acetic acid was the best solvent, as using only 1 molpercent Pd/C provided piperidine quantitatively. Substrate scope analysis and density functional theory calculations indicated that reaction rates are highly dependent on frontier molecular orbital characteristics and the steric bulkiness of substituents. Moreover, the established method was used for the concise synthesis of the anti-Alzheimer drug donepezil (Aricept?).