22065-85-6 Usage
Description
N-Benzylpiperidine-4-carboxaldehyde is an organic compound that serves as a versatile intermediate in the synthesis of various pharmaceuticals and chemical compounds. It is a colorless oil with unique chemical properties that make it suitable for a range of applications.
Uses
Used in Pharmaceutical Industry:
N-Benzylpiperidine-4-carboxaldehyde is used as a reactant for the synthesis of various pharmaceutical compounds, including:
1. Donepezil: It is used as a reactant for the synthesis of Donepezil, a drug used for the treatment of Alzheimer's disease.
2. MCH-R1 antagonists: It is also used in the synthesis of MCH-R1 antagonists, which have potential applications in the treatment of various conditions such as obesity and depression.
Used in Chemical Synthesis:
1. Stereospecific allylic alkylation: N-Benzylpiperidine-4-carboxaldehyde is used as a reactant in stereospecific allylic alkylation reactions, which are important in the synthesis of complex organic molecules with specific stereochemistry.
2. Reactions of Grignard reagents with carbonyl compounds: It is utilized in the reactions of Grignard reagents with carbonyl compounds, a widely used method for the formation of carbon-carbon bonds in organic synthesis.
3. Fluorodenitrations and nitrodehalogenations: N-Benzylpiperidine-4-carboxaldehyde is used in fluorodenitrations and nitrodehalogenations, which are essential for the synthesis of labeled PET ligands and fluoropharmaceuticals.
Used in Medicinal Chemistry:
N-Benzylpiperidine-4-carboxaldehyde is used as a selective α1 receptor antagonist, which has potential applications in the treatment of various conditions such as hypertension and benign prostatic hyperplasia.
Synthesis
A round
bottom flask was charged with oxalyl chloride (16.2 g, 0.12
mol), dichloromethane (150 mL) and anhydrous dimethyl sulfoxide
(20 mL). Stir the reaction mixture mass in a cryo bath at -70 °C
for 15 min. The resulting mixture is charged dropwise with N-benzyl piperidine alcohol 3 (20 g, 0.097 mol), along with
triethylamine (24.6 g, 0.24 mol) and continued stirring for the
next 15 min. After that, the mass is allowed to attain room
temperature overnight, then diluted with dichloromethane (100
mL) and quenched with cold water. The organic layer was
washed subsequently with 5 % HCl solution, brine solution, 5
% sodium bicarbonate solution and dried over sodium sulfate.
Toluene was removed in vacuo to afford N-Benzylpiperidine-4-carboxaldehyde (19.2 g, 96 %).
Check Digit Verification of cas no
The CAS Registry Mumber 22065-85-6 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,2,0,6 and 5 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 22065-85:
(7*2)+(6*2)+(5*0)+(4*6)+(3*5)+(2*8)+(1*5)=86
86 % 10 = 6
So 22065-85-6 is a valid CAS Registry Number.
InChI:InChI=1/C13H17NO/c15-11-13-6-8-14(9-7-13)10-12-4-2-1-3-5-12/h1-5,11,13H,6-10H2
22065-85-6Relevant articles and documents
First synthesis of racemic trans propargylamino-donepezil, a pleiotrope agent able to both inhibit AChE and MAO-B, with potential interest against Alzheimer’s disease
Guieu, Benjamin,Lecoutey, Cedric,Legay, Rémi,Davis, Audrey,De Oliveira Santos, Jana Sopkova,Altomare, Cosimo Damiano,Catto, Marco,Rochais, Christophe,Dallemagne, Patrick
, (2021)
Alzheimer’s disease (AD) is a multifactorial neurodegenerative disease towards which pleiotropic approach using Multi-Target Directed Ligands is nowadays recognized as probably convenient. Among the numerous targets which are today validated against AD, acetylcholinesterase (ACh) and Monoamine Oxidase-B (MAO-B) appear as particularly convincing, especially if displayed by a sole agent such as ladostigil, currently in clinical trial in AD. Considering these results, we wanted to take benefit of the structural analogy lying in donepezil (DPZ) and rasagiline, two indane derivatives marketed as AChE and MAO-B inhibitors, respectively, and to propose the synthesis and the preliminary in vitro biological characterization of a structural compromise between these two compounds, we called propargylaminodonepezil (PADPZ). The synthesis of racemic trans PADPZ was achieved and its biological evaluation established its inhibitory activities towards both (h)AChE (IC50 = 0.4 μM) and (h)MAO-B (IC50 = 6.4 μM).
Synthesis method of N-benzyl-4-piperidine formaldehyde
-
, (2020/08/18)
The invention belongs to the technical field of medicine synthesis, and particularly relates to a synthesis method of N-benzyl-4-piperidine formaldehyde. According to the invention, 4-piperidinecarboxylic acid is used as a raw material; an esterification reaction is carried out to generate 4-methyl piperidinecarboxylate hydrochloride; an alkylation reaction is carried out on N-benzyl-4-methyl piperidinecarboxylate hydrochloride to generate N-benzyl-4-methyl piperidinecarboxylate; n-benzyl-4-methyl piperidinecarboxylate is hydrolyzed to obtain N-benzyl-4-piperidinecarboxylic acid, N-benzyl-4-piperidinecarboxylic acid is subjected to an acylation reaction to generate N-benzyl-4-piperidinecarboxamide, N-benzyl-4-piperidinecarboxamide is dehydrated to obtain 1-benzylpiperidine-4-nitrile, and 1-benzylpiperidine-4-nitrile is subjected to a reduction reaction to generate N-benzyl-4-piperidineformaldehyde. The method is mild in reaction condition, simple in aftertreatment and high in yield, N-benzyl-4-piperidinecarboxaldehyde can be obtained at the high yield at the temperature of 0 DEG C, column chromatography is not needed, and repeatability is high.
SMALL MOLECULE INHIBITORS OF THE BFRB:BFD INTERACTION
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Paragraph 0195, (2020/07/05)
The present technology provides compounds of Formula I and related methods for treating a bacterial infection as well as methods for inhibiting interaction of a bacterioferritin and a bacterioferritin-associated ferredoxin.