90670-04-5

Basic information

• Product Name: Piperidine, 1-benzoyl-4-chloro-
• CAS NO: 90670-04-5
• Molecular Formula: C12H14ClNO
• Molecular Weight: 223.702
• Mol File: 90670-04-5.mol

Chemical Properties

• CAS DataBase Reference: Piperidine, 1-benzoyl-4-chloro-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1-benzoyl-4-chloro-(90670-04-5)
• EPA Substance Registry System: Piperidine, 1-benzoyl-4-chloro-(90670-04-5)

Safety Data

• Hazardous Substances Data: 90670-04-5(Hazardous Substances Data)

Upstream product

• 58748-24-6 N-Cyclododecylmorpholine 
• 90670-03-4 N-Benzoyl-4-piperidinopiperidine 
• 107264-22-2 C₂₆H₂₄N₂O₃ 
• 98-88-4 benzoyl chloride 
• 3725-39-1 N-(cylododec-1-enyl)-morpholine 
• 5274-99-7 1-benzoylisonipecotic acid 
• 80213-01-0 (4-hydroxy-1-piperidinyl)(phenyl)methanone 
• 5382-16-1 4-HYDROXYPIPERIDINE 

Relevant articles and documents

Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation

A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.

Silver-catalyzed decarboxylative chlorination of aliphatic carboxylic acids

Decarboxylative halogenation of carboxylic acids, the Hunsdiecker reaction, is one of the fundamental functional group transformations in organic chemistry. As the initial method requires the preparations of strictly anhydrous silver carboxylates, several modifications have been developed to simplify the procedures. However, these methods suffer from the use of highly toxic reagents, harsh reaction conditions, or limited scope of application. In addition, none is catalytic for aliphatic carboxylic acids. In this Article, we report the first catalytic Hunsdiecker reaction of aliphatic carboxylic acids. Thus, with the catalysis of Ag(Phen)2OTf, the reactions of carboxylic acids with t-butyl hypochlorite afforded the corresponding chlorodecarboxylation products in high yields under mild conditions. This method is not only efficient and general, but also chemoselective. Moreover, it exhibits remarkable functional group compatibility, making it of more practical value in organic synthesis. The mechanism of single electron transfer followed by chlorine atom transfer is proposed for the catalytic chlorodecarboxylation.

PHOTODECARBOXYLATIVE CHLORINATION OF CARBOXYLIC ACIDS VIA THEIR BENZOPHENONE OXIME ESTERS

Decarboxylative chlorination of various aromatic and aliphatic carboxylic acids is performed successfully by the photolysis of their benzophenone oxime esters in carbon tetrachloride and corresponding chloro compounds are prepared in good yields.High selective generation of the certain radical and efficiency of the stable radical precursor, benzophenone oxime ester, afford much advantage for radical chemistry.

Tests of a Piperidino Mask for the Protection of Functionalized Carbon Sites in Multistep Syntheses

Primary alkyl chlorides (R-Cl) are easily isolated in excellent yield after treatment of the appropriate N-alkylpiperidines (R-NC5H10) with α-chloroethyl chloroformate.The method is exemplified by the conversion of a variety of alkylpiperidines, including systems with other sensitive functionalities, to the respective chlorides in yields varying from 90 to 97percent.The potential significance of this process in drug congener preparation and in total synthesis is outlined.Similar fragmentations of N-sec-alkylpiperidines are described.