83709-88-0

Basic information

• Product Name: 2-methyl-6-undecylpiperidine
• Synonyms: Piperidine, 2-methyl-6-undecyl-
• CAS NO: 83709-88-0
• Molecular Formula: C₁₇H₃₅N
• Molecular Weight: 253.4665
• Mol File: 83709-88-0.mol

Chemical Properties

• Boiling Point: 320.1°C at 760 mmHg
• Flash Point: 150.9°C
• Density: 0.821g/cm³
• Vapor Pressure: 0.000324mmHg at 25°C
• Refractive Index: 1.445
• CAS DataBase Reference: 2-methyl-6-undecylpiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-methyl-6-undecylpiperidine(83709-88-0)
• EPA Substance Registry System: 2-methyl-6-undecylpiperidine(83709-88-0)

Safety Data

• Hazardous Substances Data: 83709-88-0(Hazardous Substances Data)

Upstream product

• 160549-82-6 tert-butyl (2R,6R)-(-)-2-methyl-6-undecyl-piperidine-1-carboxylate 
• 917-54-4 methyllithium 
• 503843-27-4 (2R,6R)-[(1R)-2-hydroxy-1-phenylethyl]-2-methyl-6-undecylpiperidine 
• 111512-38-0 4,8-dihydroxy-1,10-undecanediene 
• 184535-10-2 (2S,6R)-2-allyl-6-methylpiperidine-1-carboxylic acid tert-butyl ester 
• 693-67-4 bromoundecane 
• 6280-87-1 δ-chlorovaleronitrile 
• 95018-40-9 6-Undecyl-2,3,4,5-tetrahydropyridine 
• 160549-81-5 N-Boc-2(R)-undecylpiperidine 
• 101572-32-1 2-dodecanoylcyclopentanone 
• 159425-00-0 ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((2R,6R)-1-hydroxy-6-undecyl-piperidin-2-yl)-methanone 
• 159425-09-9 ((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-((R)-1-oxy-6-undecyl-2,3,4,5-tetrahydro-pyridin-2-yl)-methanone 
• 159425-06-6 1-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-5-(2-undecyl-[1,3]dioxolan-2-yl)-pentan-1-one 
• 117286-10-9 undecylmagnesium bromide 

Relevant articles and documents

Hydrogenation of Pyridines Using a Nitrogen-Modified Titania-Supported Cobalt Catalyst

Novel heterogeneous catalysts were prepared by impregnation of titania with a solution of cobalt acetate/melamine and subsequent pyrolysis. The resulting materials show an unusual nitrogen-modified titanium structure through partial implementation of nitrogen into the support. The optimal catalyst displayed good activity and selectivity for challenging pyridine hydrogenation under acid free conditions in water as solvent.

Stereoselective synthesis of 2,6-: Trans -4-oxopiperidines using an acid-mediated 6- endo-trig cyclisation

An acid-mediated 6-endo-trig cyclisation of amine-substituted enones has been developed for the stereoselective synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines. Performed under conditions that prevent removal of the Boc-protecting group or acetal formation, the key cyclisation was found to generate cleanly the 4-oxopiperidine products in high overall yields from a wide range of alkyl substituted enones. The synthetic utility of the trans-6-alkyl-2-methyl-4-oxopiperidines formed from this process was demonstrated with the total synthesis of the quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (-)-solenopsin A.

Removal of the pyridine directing group from α-substituted N-(pyridin-2-yl)piperidines obtained via directed Ru-catalyzed sp3 C-H functionalization

Two strategies, "hydrogenation-hydride reduction" and "quaternization-hydride reduction", are reported that make use of mild reaction conditions (room temperature) to efficiently remove the N-pyridin-2-yl directing group from a diverse set of C-2-substituted piperidines that were synthesized through directed Ru-catalyzed sp3 C-H functionalization. The deprotected products are obtained in moderate to good overall yields irrespective of the strategy followed, indicating that both methods are generally equally effective. Only in the case of 2,6-disubstituted piperidines, could the "quaternization-hydride reduction" strategy not be used. The "hydrogenation-hydride reduction" protocol was successfully applied to trans- and cis-2-methyl-N-(pyridin-2-yl)-6-undecylpiperidine in a short synthetic route toward (±)-solenopsin A (trans diastereoisomer) and (±)-isosolenopsin A (cis diastereoisomer). The absolute configuration of the enantiomers of these fire ant alkaloids could be determined via VCD spectroscopy.

Modified fry cyanation of a chiral pyridinium salt: Asymmetric syntheses of (-)-coniine and (-)-solenopsin A

The synthesis of chiral 2-cyano-Δ4-tetrahydropyridine 5 was carried out in 85 % yield through a modified two-step Fry reductive cyanation of pyridinium salt (+)-3c that used lithium triethylborohydride as the hydride donor. An alkylation-reduction sequence provided 2-alkyl-substituted tetrahydropyridines (+)-10a and (+)-10b in 72-75 % yield after chromatographic purification. This protocol has been applied to the asymmetric syntheses of piperidine alkaloids (-)-coniine and (-)-solenopsin A. The two-step reductive cyanation of chiral pyridinium salt (+)-3c afforded α-amino nitrile 5 in 85 % yield, which underwent an alkylation-reduction sequence followed by removal of the chiral moiety to yield the hemlock alkaloid (-)-coniine as its mandelate salt (>99:1 er). This reaction sequence was also used for the synthesis of the trans-2,6-disubstituted piperidine alkaloid (-)-solenopsin A. Copyright

Access to 2,6-disubstituted piperidines: Control of the diastereoselectivity, scope, and limitations. applications to the stereoselective synthesis of (-)-solenopsine A and alkaloid (+)-241D

Scope and limitations in the diastereoselective preparation of 2,6-cis or 2,6-trans disubstituted piperidines are described, through intramolecular reaction of chiral β′-carbamate-α,β-unsaturated ketone. This methodology has been applied to the total synthesis of a few well chosen examples, such as (-)-solenopsine A and alkaloid (+)-241D.

Rapid configuration analysis of the solenopsins

A protocol for rapid access to the relative and absolute configurations of the solenopsins, the venom alkaloids of fire ants (Solenopsis spp.), was developed based on chiral capillary gas chromatography. The synthesis of racemic mixtures of 2-methyl-6-alkylpiperidines and the isolation of natural (2R,6R)- and (2R,6S)-2-methyl-6-undecylpiperidines allowed for the standardization of the chromatographic method. Application of this protocol revealed the previously unknown natural occurrence of four stereoisomers of 2-methyl-6-undecylpiperidine in venom samples from workers and gynes of Solenopsis saevissima.

Synthesis of enantiomerically pure fire ant venom alkaloids: Solenopsins and isosolenopsins A, B and C

(Chemical Equation Presented) Concise and efficient methods for the synthesis of enantiomers of fire ant venom alkaloids solenopsin and isosolenopsin A, B, and C are described. These syntheses are based on diastereoselective electrophilic substitution of enatiomerically-pure α-lithiated 2-alkylpiperidine.

A new route to trans-2,6-disubstituted piperidine-related alkaloids using a novel C2-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester

A novel C2-symmetric 2,6-diallylpiperidine carboxylic acid methyl ester 1 was prepared by the double asymmetric allylboration of glutaldehyde followed by an aminocyclization and carbamation. On the basis of desymmetrization of 1 using iodocarbamation, one allyl group of 1 was protected and monofunctionalizations of the resulting oxazolidinone 11 were performed. The reaction of the N-methoxycarbonyl piperidine 25 employing decarbamation reagent (n-PrSLi or TMSI) as a key step gave oxazolidinone 26 or 17 including an intramolecular ring formation, which was transformed in a few steps into (-)-porantheridine (2) and (-)-2-epi-porantheridine (3), respectively. In addition, the expedient synthesis of (+)-epi-dihydropinidine (4), (2R,6R)-trans-solenopsin A (5), and precoccinelline (6), starting from 11 is described. The Royal Society of Chemistry 2006.

Tandem overman rearrangement and intramolecular amidomercuration reactions. Stereocontrolled synthesis of cis- and frans-2,6-dialkylpiperidines

(Chemical Equation Presented) Hg(II)-mediated tandem Overman rearrangement and intramolecular amidomercuration reactions were proven to provide a convenient tool for the stereoselective synthesis of cis- and frans-2,6-disubstituted piperidines. Thus, upon treatment with Hg(OTFA) 2 in THF, the trichloroacetimidate 1 directly transformed into the 2,6-dialkyl piperidine 2 with almost exclusive trans selectivity. The amiodomercuration reaction of the carbamate 7 by Hg(OTFA)2 in nitromethane showed an excellent cis selectivity. Also reported is the stereoselective synthesis of solenopsin A and isosolenopsin A.

Dearomatization of N-phenyl-2,6-dialkylpiperidines: Practical synthesis of (±)-solenopsin A and (±)-dihydropinidine

The fire ant venom alkaloid (±)-solenopsin A was prepared in 4 steps (34%) starting from the N-phenyl-2-undecyl piperidine (1c). The key step in this synthesis involved the dearomatization of the phenyl group of N-phenyl-2-methyl-6-undecyl-piperidine (9c), which was carried out under Birch conditions.