955050-02-9

Basic information

• Product Name: tert-butyl 4-benzamidopiperidine-1-carboxylate
• Synonyms: tert-butyl 4-benzamidopiperidine-1-carboxylate
• CAS NO: 955050-02-9
• Molecular Weight: 304.389
• Mol File: 955050-02-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: tert-butyl 4-benzamidopiperidine-1-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 4-benzamidopiperidine-1-carboxylate(955050-02-9)
• EPA Substance Registry System: tert-butyl 4-benzamidopiperidine-1-carboxylate(955050-02-9)

Safety Data

• Hazardous Substances Data: 955050-02-9(Hazardous Substances Data)

Upstream product

• 93-58-3 benzoic acid methyl ester 
• 87120-72-7 1-(tert-butoxycarbonyl)-4-aminopiperidine 
• 65-85-0 benzoic acid 
• 98-88-4 benzoyl chloride 

Downstream Products

• 33953-37-6 N-(piperidin-4-yl)benzamide 

Relevant articles and documents

A practical and sustainable protocol for direct amidation of unactivated esters under transition-metal-free and solvent-free conditions

In this paper, a NaOtBu-mediated synthesis approach was developed for direct amidation of unactivated esters with amines under transition-metal-free and solvent-free conditions, affording a series of amides in good to excellent yields at room temperature. In particular, an environmentally friendly and practical workup procedure, which circumvents the use of organic solvents and chromatography in most cases, was disclosed. Moreover, the gram-scale production of representative products3a,3wand3auwas efficiently realized by applying operationally simple, sustainable and practical procedures. Furthermore, this approach was also applicable to the synthesis of valuable molecules such as moclobemide (a powerful antidepressant), benodanil and fenfuram (two commercial agricultural fungicides). These results demonstrate that this protocol has the potential to streamline amide synthesis in industry. Meanwhile, quantitative green metrics of all the target products were evaluated, implying that the present protocol is advantageous over the reported ones in terms of environmental friendliness and sustainability. Finally, additional experiments and computational calculations were carried out to elucidate the mechanistic insight of this transformation, and one plausible mechanism was provided on the basis of these results and the related literature reports.

Evaluation of alternative solvents in common amide coupling reactions: Replacement of dichloromethane and N,N-dimethylformamide

A range of alternative solvents have been evaluated within amidation reactions employing common coupling reagents with a view to identifying suitable replacements for dichloromethane and N,N-dimethylformamide.