17642-89-6

Basic information

• Product Name: 2-Piperidinethione, 1-(phenylmethyl)-
• Synonyms: 2-Piperidinethione, 1-(phenylmethyl)-
• CAS NO: 17642-89-6
• Molecular Formula: C₁₂H₁₅NS
• Molecular Weight: 0
• Mol File: 17642-89-6.mol
• Article Data: 6

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Piperidinethione, 1-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Piperidinethione, 1-(phenylmethyl)-(17642-89-6)
• EPA Substance Registry System: 2-Piperidinethione, 1-(phenylmethyl)-(17642-89-6)

Safety Data

• Hazardous Substances Data: 17642-89-6(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 675-20-7 piperidin-2-one 
• 4783-65-7 N-benzyl-2-piperidinone 

Downstream Products

• 36939-29-4 (+/-)-1-benzyl-2-phenylpiperidine 
• 1017238-01-5 1-benzyl-2,2-dibutylpiperidine 
• 1228468-96-9 1-benzyl-2,2-diethylpiperidine 
• 1381774-27-1 C₁₆H₂₃NOS 
• 1381774-26-0 C₁₆H₂₃NOS 
• 1381774-29-3 (S)-3-((R)-1-hydroxy-2-methylpropyl)-1-(4-methoxyphenyl)piperidine-2-thione 
• 1381774-28-2 (S)-3-((S)-1-hydroxy-2-methylpropyl)-1-(4-methoxyphenyl)piperidine-2-thione 
• 1144516-43-7 Br^(1-)*C₂₀H₂₂NOS⁽¹⁺⁾ 
• 3238-60-6 rac-coniine 

Relevant articles and documents

Reductive Alkylation of Tertiary Lactams via Addition of Organocopper (RCu) Reagents to Thioiminium Ions

A simple procedure for the conversion of tertiary lactams to 2-monoalkylated cyclic amines is described. The reaction sequence involves conversion of a lactam to a thioiminium ion followed by reaction with an organocopper (RCu) reagent and final reduction with triacetoxyborohydride. The reaction is high yielding and shows an excellent functional group tolerance. Its utility is demonstrated by a rapid synthesis of indolizidine 167B. The excellent chemoselectivity of the process, where only monoalkylation products are formed, is rationalized by a mechanism involving the formation of a transient enamine.

Studies on the Eschenmoser coupling reaction and insights on its mechanism. Application in the synthesis of Norallosedamine and other alkaloids

The conditions of the Eschenmoser coupling reaction were studied. The formation of the α-thioiminium ion was achieved faster in the presence of an additive (NaI) and dry chloroform as the preferred solvent. The developed conditions were used for the second part of the reaction (the sulfur extrusion itself). The present protocol avoids the formation of byproducts, which were previously described as a major drawback to be overcome. Electrospray ionization tandem mass spectrometry was used to characterize some aspects (intermediates) of the first step of the reaction mechanism. Some reduction conditions were properly tested and the selected conditions were applied to the synthesis of the natural alkaloid Norallosedamine and other derivatives.

Ultrasound in Heterogeneous Organic Reactions. An Improved Procedure for the Synthesis of Thioamides

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