205641-99-2

Basic information

• Product Name: Piperidine, 1-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-
• CAS NO: 205641-99-2
• Molecular Formula: C19H23NO2S
• Molecular Weight: 329.463
• Mol File: 205641-99-2.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Piperidine, 1-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Piperidine, 1-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-(205641-99-2)
• EPA Substance Registry System: Piperidine, 1-[(4-methylphenyl)sulfonyl]-4-(phenylmethyl)-(205641-99-2)

Safety Data

• Hazardous Substances Data: 205641-99-2(Hazardous Substances Data)

Upstream product

• 31252-42-3 4-benzylpyperidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 2181-21-7 1-[(4-methylbenzene)sulfonyl]-4-methylidenepiperidine 
• 98-80-6 phenylboronic acid 

Downstream Products

• 31252-42-3 4-benzylpyperidine 

Relevant articles and documents

An efficient route to 4-(substituted benzyl)piperidines

A novel approach to 4-(substituted benzyl)piperidines has been developed. The key steps involve the cyclization of imines bearing an allylsilane in the side-chain followed by the palladium-catalyzed cross-coupling of the resulting 4-methylenepiperidine with organoboronic acids under an atmosphere of oxygen.

METHOD FOR DEPROTECTING ARYL OR ALKYL SULFONAMIDES OF PRIMARY OR SECONDARY AMINES

The invention relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by contacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material in the presence of a solid proton source under conditions sufficient to form the corresponding amine. The invention also relates to a method for removing an alkyl sulfonyl or aryl sulfonyl protecting group from a primary or secondary amine by a) reacting an alkyl sulfonamide or an aryl sulfonamide with a Stage 0 or Stage I alkali metal-silica gel material, and b) subsequently reacting the reaction product from step a) with an electrophile or a proton source. Preferred Stage 0 or Stage I alkali metal-silica gel materials include Na, K2Na, and Na2K.

Cleavage of sulfonamides with phenyldimethylsilyllithium

The toluene-p-sulfonamides of secondary amines and indoles are cleaved by treatment with phenyldimethylsilyllithium to give the secondary amines. Aziridine toluene-p-sulfonamides, however, are opened by attack of the silyllithium reagent on carbon to give β-silylethyl sulfonamides. The aziridine toluene-p-sulfonamide 22 derived from norbornene is different in giving the 2-[dimethyl(phenyl)silyl]-4-methylbenzenesulfonamide 23 of exo-norbornylamine. The aziridine toluene-p-sulfonamides 26, 28 and 30, derived from methyl cinnamate, methyl acrylate and cinnamyl acetate, are also anomalous, giving 3-[N-(p-tolylsulfonyl)amino]-3-phenylpropionic acid 27, {3-[N-(p-tolylsulfonyl)amino]propionyl}-dimethyl(phenyl)silane 29 and trans-cinnamyl alcohol 31, respectively, each derived by opening of the aziridine ring followed by loss of the silyl group.