92321-27-2

Basic information

• Product Name: 2,6-dimethyl-N-benzylpiperidine
• Synonyms: 2,6-dimethyl-N-benzylpiperidine
• CAS NO: 92321-27-2
• Molecular Weight: 203.327
• Mol File: 92321-27-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 2,6-dimethyl-N-benzylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-dimethyl-N-benzylpiperidine(92321-27-2)
• EPA Substance Registry System: 2,6-dimethyl-N-benzylpiperidine(92321-27-2)

Safety Data

• Hazardous Substances Data: 92321-27-2(Hazardous Substances Data)

Upstream product

• 98195-08-5 1-benzyl-2,6-dicyanopiperidine 
• 98195-16-5 (2S,6S)-1-Benzyl-2,6-dimethyl-piperidine-2,6-dicarbonitrile 
• 13505-34-5 2,6-heptandione 
• 100-44-7 benzyl chloride 
• 504-03-0 2.6-dimethylpiperidine 
• 100-46-9 benzylamine 
• 98-88-4 benzoyl chloride 
• 20722-53-6 1-benzoyl-2,6-dimethyl-piperidine 
• 98195-09-6 1-benzyl-2,6-dicyano-2-methylpiperidine 
• 126216-53-3 C₂₄H₂₃N₇ 
• 98195-16-5 1-benzyl-2,6-dicyano-2,6-dimethylpiperidine 

Relevant articles and documents

A Manganese Pre-Catalyst: Mild Reduction of Amides, Ketones, Aldehydes, and Esters

A new (N-phosphinoamidinate)manganese complex is shown to be a useful pre-catalyst for the hydrosilative reduction of carbonyl compounds, and in most cases at room temperature. The Mn-catalyzed reduction of tertiary amides to tertiary amines, with a useful scope, is demonstrated for the first time by use of this catalyst, and is competitive with the most effective transition-metal catalysts known for such transformations. Ketones, aldehydes, and esters were also successfully reduced under mild conditions by using this new Mn catalyst.

Diastereoselective synthesis of 2,5-dimethylpyrrolidines and 2,6- dimethylpiperidines by reductive amination of 2,5-hexanedione and 2,6- heptanedione with hydride reagents

The reductive amination of 2,5-hexanedione and 2,6-heptanedione with ammonia and primary amines in the presence of hydride reagents afforded 2,5- dimethylpyrrolidines and 2,6-dimethylpiperidines with variable diastereoselectivity, as the cis/trans ratio was affected by the size of the ring formed and the steric and electronic properties of the nitrogen substituent. Increasing the bulkiness of the nitrogen substituent, the cis pyrrolidines and the trans-piperidines were obtained with enhanced selectivity.

Benzotriazole: A novel synthetic auxiliary

Benzotriazole and aldehydes react reversibly to give addition products: in the presence of amines and other NH-compounds water can be eliminated to form products of type Bt-CHR-NR′R″. The latter are versatile intermediates for the preparation of primary, secondary, and tertiary amines and in the alkylation of hydroxylamines, hydrazines, amides, thioamides, and sulfonamides. Polyfunctional amines and other polyfunctional compounds can also be prepared, and they enable significant extending of Mannich reaction. Similar oxygen compounds Bt-CRR′-OR″ enable new syntheses of ethers and esters. Reactions in which benzotriazole is eliminated rather than substituted open up new pathways to enamines, enol ethers, and nitrones. The methodology is capable of extension to a variety of vinylogous systems including benzenoid and heteroaromatic derivatives. In addition to acting as a versatile leaving group, benzotriazolyl residues activate neighboring CH bonds to proton loss and a variety of such applications is described.