Intermediate of API

22065-85-6

  • Product Name：N-Benzylpiperidine-4-carboxaldehyde
  • Molecular Formula：C13H17NO
  • Specifications：99%
  • Molecular Weight：203.284
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Product Details;

CasNo： 22065-85-6

Molecular Formula： C13H17NO

Appearance： colorless oil

Great Price Factory Supply High Purity 99% N-Benzylpiperidine-4-carboxaldehyde 22065-85-6

  • Molecular Formula:C13H17NO
  • Molecular Weight:203.284
  • Appearance/Colour:colorless oil 
  • Vapor Pressure:0.00119mmHg at 25°C 
  • Melting Point:315 
  • Refractive Index:n20/D 1.537  
  • Boiling Point:299.5 °C at 760 mmHg 
  • PKA:8.04±0.10(Predicted) 
  • Flash Point:104.3 °C 
  • PSA：20.31000 
  • Density:1.114 g/cm3 
  • LogP:2.03540 

N-Benzylpiperidine-4-carboxaldehyde(Cas 22065-85-6) Usage

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 %).

Chemical Properties

Colorless Oil

Uses

Reactant for:Stereospecific allylic alkylationReactions of Grignard reagents with carbonyl compoundsFluorodenitrations and nitrodehalogenations for labeled PET ligands and fluoropharmaceuticalsSelective α1 receptor antagonistsReactant for synthesis of:DonepezilMCH-R1 antagonists

IUPAC Name: 1-benzylpiperidine-4-carbaldehyde  
Isomeric SMILES: C1CN(CCC1C=O)CC2=CC=CC=C2  
InChIKey: SGIBOXBBPQRZDM-UHFFFAOYSA-N  
InChI: InChI=1S/C13H17NO/c15-11-13-6-8-14(9-7-13)10-12-4-2-1-3-5-12/h1-5,11,13H,6-10H2  

22065-85-6 Relevant articles

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 multifacto...

New approach to N-substituted-1,2,3,6-tetrahydro-pyridine-4-carbaldehyde, a precursor for synthesizing Aricept, isoguvacine, and deethylibophyllidine

Tsai, Min-Ruei,Sun, Pei-Pei,Chang, Meng-Yang,Changa, Nein-Chen

, p. 613 - 617 (2004)

A new route towards the synthesis of N-s...

Design, synthesis, and evaluation of donepezil-like compounds as AChE and BACE-1 inhibitors

Paola Costanzo†, Luca Cariati†, Doriana Desiderio‡, Roberta Sgammato§∥, Anna Lamberti§, Rosaria Arcone§∥, Raffaele Salerno†, Monica Nardi⊥, Mariorosario Masullo§∥, and Manuela Oliverio*†

, ACS Med. Chem. Lett. 2016, 7, 5, 470–475

… available N-benzylpiperidine-4-carboxaldehyde 10 was … the synthesis of N-benzylpiperidine-4-carboxaldehyde 12 from … nucleus and N-benzylpiperidine-4-carboxaldehyde derivatives …

Small Molecule Inhibitors of the BfrB-Bfd Interaction Decrease Pseudomonas aeruginosa Fitness and Potentiate Fluoroquinolone Activity

Hewage, Achala N. D. Punchi,Yao, Huili,Nammalwar, Baskar,Gnanasekaran, Krishna Kumar,Lovell, Scott,Bunce, Richard A.,Eshelman, Kate,Phaniraj, Sahishna M.,Lee, Molly M.,Peterson, Blake R.,Battaile, Kevin P.,Reitz, Allen B.,Rivera, Mario

supporting information, p. 8171 - 8184 (2019/06/13)

The iron storage protein bacterioferriti...

22065-85-6 Process route

1-benzylpiperidine-4-carboxylic acid methyl ester
10315-06-7

1-benzylpiperidine-4-carboxylic acid methyl ester

N-benzyl-4-formylpiperidine
22065-85-6

N-benzyl-4-formylpiperidine

Conditions
Conditions Yield
With red-aluminum/morpholine complex; In toluene; at -5 - 0 ℃; for 0.5h; Reagent/catalyst; Solvent; Inert atmosphere; Large scale;
96.5%
Multi-step reaction with 2 steps
1: 69.5 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 50 °C
2: 94.3 percent / oxalyl chloride; dimethyl sulfoxide; Et3N / CH2Cl2 / 0.25 h / -55 °C
With lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; 1: Reduction / 2: Swern oxidation;
 
Multi-step reaction with 4 steps
1.1: water; methanol; sodium hydroxide / 2 h / Reflux
2.1: thionyl chloride / 2 h / Reflux
2.2: 0.5 h / Cooling with ice
3.1: thionyl chloride / 5 h / Reflux
4.1: diisobutylaluminium hydride / toluene / 1 h / 0 °C
4.2: 0.5 h / pH 8
With methanol; thionyl chloride; water; diisobutylaluminium hydride; sodium hydroxide; In toluene;
 
1-benzylpiperidine-4-carbonitrile
62718-31-4

1-benzylpiperidine-4-carbonitrile

N-benzyl-4-formylpiperidine
22065-85-6

N-benzyl-4-formylpiperidine

Conditions
Conditions Yield
1-benzylpiperidine-4-carbonitrile; With diisobutylaluminium hydride; In toluene; at 0 ℃; for 1h;
With water; sodium hydroxide; In methanol; toluene; for 0.5h; pH=8; Temperature;
97.5%

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