N-benzoyl-2-piperidinecarboxaldehyde

Base Information

• Chemical Name: N-benzoyl-2-piperidinecarboxaldehyde
• CAS No.: 133787-01-6
• Molecular Formula: C₁₃H₁₅NO₂
• Molecular Weight: 217.268
• Mol file: 133787-01-6.mol

Synonyms:N-benzoyl-2-piperidinecarboxaldehyde

Chemical Property of N-benzoyl-2-piperidinecarboxaldehyde

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzoyl-2-piperidinecarboxaldehyde

There total 4 articles about N-benzoyl-2-piperidinecarboxaldehyde which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

N-benzoyl-2-(hydroxymethyl)piperidine (92041-11-7) → N-benzoyl-2-piperidinecarboxaldehyde (133787-01-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; Schlenk technique;

DOI:10.1002/chem.202101035

Reference yield: 61.0%

(5,6-dihydropyridin-1(2H)-yl)(phenyl)methanone (71785-91-6) + carbon monoxide (201230-82-2) → N-benzoylpiperidine (776-75-0) + N-benzoyl-2-piperidinecarboxaldehyde (133787-01-6) + N-benzoyl-2-piperidinecarboxylic acid (78348-46-6)

Guidance literature:

With hydrogen; bis-triphenylphosphine-palladium(II) chloride; dicobalt octacarbonyl; In tetrahydrofuran; water; at 110 ℃; for 24h; under 120 Torr; Yields of byproduct given;

DOI:10.1246/bcsj.64.620

Reference yield:

methyl N-benzoyl-2-piperidine carboxylate (99720-01-1) → N-benzoyl-2-piperidinecarboxaldehyde (133787-01-6)

Guidance literature:

Multi-step reaction with 2 steps

1: zinc(II) chloride; sodium tetrahydroborate / tetrahydrofuran / 0 - 60 °C / Schlenk technique

2: Dess-Martin periodane / dichloromethane / Schlenk technique

With sodium tetrahydroborate; Dess-Martin periodane; zinc(II) chloride; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.202101035

upstream raw materials:

(5,6-dihydropyridin-1(2H)-yl)(phenyl)methanone

carbon monoxide

N-benzoyl-2-(hydroxymethyl)piperidine

methyl N-benzoyl-2-piperidine carboxylate

Downstream raw materials:

methyl (S)-1-benzoylpiperidine-2-carboxylate

N-benzoyl-(2R)-(methoxycarbonyl)piperidine

(2S)-N-benzoylpiperidine-2-carboxaldehyde dimethylacetal

N-benzoyl-2-piperidinecarboxaldehyde

Refernces

• 1、 Li, Tingting,Hammond, Gerald B.,Xu, Bo. "Cobalt-Catalyzed Aerobic Oxidative Cleavage of Alkyl Aldehydes: Synthesis of Ketones, Esters, Amides, and α-Ketoamides". supporting information. p. 9737 - 9741. Retrieved 2021/05/31.
• 2、 Minato, Daishirou,Nagasue, Yoko,Demizu, Yosuke,Onomura, Osamu. "Effecient kinetic resolution of racemic amino aldehydes by oxidation with N-iodosuccinimide". supporting information; experimental part. p. 9458 - 9461. Retrieved 2009/05/06.