63587-45-1

Basic information

• Product Name: 2-Piperidinemethanol, 1-[(4-methylphenyl)sulfonyl]-, 4-methylbenzenesulfonate (ester)
• CAS NO: 63587-45-1
• Molecular Formula: C20H25NO5S2
• Molecular Weight: 423.554
• Mol File: 63587-45-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2-Piperidinemethanol, 1-[(4-methylphenyl)sulfonyl]-, 4-methylbenzenesulfonate (ester)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Piperidinemethanol, 1-[(4-methylphenyl)sulfonyl]-, 4-methylbenzenesulfonate (ester)(63587-45-1)
• EPA Substance Registry System: 2-Piperidinemethanol, 1-[(4-methylphenyl)sulfonyl]-, 4-methylbenzenesulfonate (ester)(63587-45-1)

Safety Data

• Hazardous Substances Data: 63587-45-1(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 3433-37-2 piperidin-2-ylmethanol 

Downstream Products

• 186790-30-7 Dipropyl-[1-(toluene-4-sulfonyl)-piperidin-2-ylmethyl]-amine 
• 118290-26-9 AF-DX 384 
• 118289-11-5 (+/-)-2-[2-(N',N'-dipropylaminomethyl)piperidin-1-yl]-ethan-1-amine 
• 120990-90-1 2-<(N,N-Dipropylamino)methyl>piperidine 

Relevant articles and documents

Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems

Cyclic enamines are important synthons for many synthetic and pharmacological targets. Here, we report an inexpensive, catalyst-free, multigram-scale synthesis for cyclic enamines with exocyclic double bonds and four- to seven-membered rings. This strategy is more conducive to scale up, permissive of functionalization around the cyclic system, and less sensitive to the nature of the N-protecting group than previously-described methods for cyclic enamine synthesis. Further, we explore application of these enamines to the synthesis of highly-strained spirocyclic 3N-cyclopropyl scaffolds.

Syntheses of piperidine and perhydroazepine derivatives, precursors of two selective antagonists of muscarinic M2 receptors: AF-DX 384 and its perhydroazepine isomer

Several routes to the synthesis of the polyamines 2a and 2b required for the preparation of the muscarinic antagonists AF-DX 384 1a and its perhydroazepine isomer 1b respectively have been developed and compared. Piperidine 2a has been obtained in 4 steps in 13-15% overall yield from 2-(chloromethyl)-pyridine 3. The perhydroazepine 2b has been prepared in 4 steps in 49% overall yield from 3-aminolactam 7. Transformations of piperidinemethanol 11 afford exclusively compound 2a (5 steps, 17-20% overall yield), via the N-tosylpiperidine 12, but lead to a 1:1 mixture of isomers 2a and 2b (4 steps, 15-20% overall yield for compounds 2a and 2b) via the N-(cyanomethyl)piperidine 15. Limitations to the ring enlargement of piperidine derivatives as a function of the heterocyclic nitrogen substituent are defined.