220031-61-8

Basic information

• Product Name: tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate
• Synonyms: tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate
• CAS NO: 220031-61-8
• Molecular Weight: 304.433
• Mol File: 220031-61-8.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate(220031-61-8)
• EPA Substance Registry System: tert-butyl (1-benzylpiperidin-3-yl)methylcarbamate(220031-61-8)

Safety Data

• Hazardous Substances Data: 220031-61-8(Hazardous Substances Data)

Upstream product

• 1378312-69-6 (±)-1-benzoylpiperidine-3-carboxamide 
• 24424-99-5 di-tert-butyl dicarbonate 
• 124257-62-1 (±)-(1-benzylpiperidin-3-yl)methanamine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 142643-29-6 tert-butyl (piperidin-3-ylmethyl)carbamate 

Relevant articles and documents

The Magic of Crystal Structure-Based Inhibitor Optimization: Development of a Butyrylcholinesterase Inhibitor with Picomolar Affinity and in Vivo Activity

The enzymatic activity of butyrylcholinesterase (BChE) in the brain increases with the progression of Alzheimer's disease, thus classifying BChE as a promising drug target in advanced Alzheimer's disease. We used structure-based drug discovery approaches to develop potent, selective, and reversible human BChE inhibitors. The most potent, compound 3, had a picomolar inhibition constant versus BChE due to strong cation-π interactions, as revealed by the solved crystal structure of its complex with human BChE. Additionally, compound 3 inhibits BChE ex vivo and is noncytotoxic. In vitro pharmacokinetic experiments show that compound 3 is highly protein bound, highly permeable, and metabolically stable. Finally, compound 3 crosses the blood-brain barrier, and it improves memory, cognitive functions, and learning abilities of mice in a scopolamine model of dementia. Compound 3 is thus a promising advanced lead compound for the development of drugs for alleviating symptoms of cholinergic hypofunction in patients with advanced Alzheimer's disease.

Straightforward synthesis of orthogonally protected piperidin-3- ylmethanamine and piperidin-4-ylmethanamine derivatives

The 1,3- and 1,4-disubstituted piperidines are important building blocks in medicinal chemistry and drug discovery. We present the synthesis of orthogonally protected piperidin-3-ylmethanamine and piperidin-4-ylmethanamine derivatives from commercially available nipecotamide, isonipecotamide, nipecotic acid and isonipecotic acid. This is a straightforward two-step procedure that gives high overall yields. Purification of the intermediates using this procedure is not necessary, and the final compounds are purified by simple flash column chromatography.