120014-07-5 Usage
Description
1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine is a complex organic compound with a unique molecular structure. It is characterized by its benzyl and piperidine moieties, along with a 5,6-dimethoxy-1-oxoindan-2-ylindenemethyl group. 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine has potential applications in the pharmaceutical industry due to its structural features and chemical properties.
Uses
Used in Pharmaceutical Industry:
1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine is used as an impurity in the synthesis of Donepezil (D531750), a drug commonly prescribed for the treatment of Alzheimer's disease. Its presence as an impurity is crucial for the development and manufacturing process of Donepezil, ensuring the quality and efficacy of the final product.
Additionally, 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine serves as an intermediate in the development of anti-Alzheimer's agents. Its unique chemical structure allows for further modification and optimization to create more effective drugs targeting the cognitive decline associated with Alzheimer's disease.
Synthesis
A solution of 5,6-dimethoxy-indanone (19 g, 0.10 mol) in methanol (8 mL) is stirred under inert
atmosphere at room temperature. Slowly add NaOH flakes
(12.8 g, 0.32 mol) followed by N-benzyl-piperidine-4-carboxaldehyde (20.2 g, 0.10 mol) to the reaction mixture. The
mixture was stirred at room temperature for 3 h and progress
of the reaction was monitored by TLC (hexane:ethyl acetate;
1:1). Once the reaction is complete, the solid formed was
filtered, washed with 5 % acetic acid and then with methanol
and dried. The obtained solid (34 g) was taken into a round
bottom flask and refluxed with DMF (50 mL). Gradually cooled
to room temperature and stirred for 2 h, filtered the solid
formed, wash with chilled methanol to afford a pale yellow
crystalline solid 1-Benzyl-4-(5,6-dimethoxy-1-oxoindan-2-ylindenemethyl)piperidine (32.0 g, 84 %); m.p.: 175-177 °C.
Check Digit Verification of cas no
The CAS Registry Mumber 120014-07-5 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,2,0,0,1 and 4 respectively; the second part has 2 digits, 0 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 120014-07:
(8*1)+(7*2)+(6*0)+(5*0)+(4*1)+(3*4)+(2*0)+(1*7)=45
45 % 10 = 5
So 120014-07-5 is a valid CAS Registry Number.
InChI:InChI=1/C24H27NO3/c1-27-22-14-19-13-20(24(26)21(19)15-23(22)28-2)12-17-8-10-25(11-9-17)16-18-6-4-3-5-7-18/h3-7,12,14-15,17H,8-11,13,16H2,1-2H3/b20-12+
120014-07-5Relevant articles and documents
An improved and efficient process for the production of donepezil hydrochloride: Substitution of sodium hydroxide for n-butyl lithium via phase transfer catalysis
Niphade, Navanath,Mali, Anil,Jagtap, Kunal,Ojha, Ramesh Chandra,Vankawala, Pravinchandra J.,Mathad, Vijayavitthal T.
, p. 731 - 735 (2008)
A simple, efficient and highly economic process for the production of donepezil hydrochloride (1), an anti-Alzheimer drug is reported. The process relies upon improved and large-scale synthesis of a key intermediate: 1-benzylpiperidine-4-carboxaldehyde (2), and the introduction of operationally simple chemistry at the penultimate stage wherein 2 is reacted with 5,6-dimethoxy indanone (3) in the presence of sodium hydroxide and a phase transfer catalyst (PTC) in a biphasic solvent to furnish the intermediate 4, which is reduced and directly treated with hydrochloric acid to furnish highly pure donepezil hydrochloride with desired polymorphic form. The improved process provides donepezil hydrochloride at considerably lower cost and allows the omission of hazardous chemicals.
Purification method of donepezil hydrochloride key intermediate compound (by machine translation)
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Paragraph 0031-0037, (2020/08/17)
The invention discloses a purification method of a donepezil hydrochloride key intermediate compound, and the crude molecular formula of the compound (I) is shown in the specification. Solid potassium fluoride (KFFFAl) on alumina2 O3 In the presence C6 -C12 In the aromatic hydrocarbon-containing organic solvent, the reaction 70 - 110 °C is stirred at 0.5 - 3h to obtain a high-purity compound (I), in C. 6 -C12 The benzene-containing aromatic hydrocarbon organic solvent is selected from benzene, toluene and xylene, is simple and convenient to operate, high in yield and good in product purity, and is suitable for industrial production. (by machine translation)
Preparation method of donepezil hydrochloride
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Paragraph 0039; 0042; 0043, (2016/10/17)
The invention discloses a preparation method of donepezil hydrochloride. The preparation method comprises the steps that 3-chlorine-1-(3, 4-dimethoxy phenyl) propane-1-ketone (II) is made to react with N-benzyl-4-formyl-piperidine (III) under the conditio