3238-60-6

Usage

Uses

Used in Pharmaceutical Industry:
2-Propylpiperidine is used as an intermediate in the synthesis of various pharmaceutical compounds. Its unique chemical structure allows it to be a versatile building block for the development of new drugs with potential applications in treating various medical conditions.
Used in Chemical Synthesis:
Due to its reactivity and solubility in organic solvents, 2-Propylpiperidine is used as a reagent in various chemical synthesis processes. It can be employed to produce a range of organic compounds, contributing to the advancement of the chemical industry.
Used in Research and Development:
2-Propylpiperidine serves as a valuable compound for research purposes, particularly in the fields of organic chemistry and medicinal chemistry. It can be used to study the properties and reactions of piperidine derivatives, leading to a better understanding of their potential applications and the development of new compounds with improved properties.

Synthesis Reference(s)

Tetrahedron Letters, 26, p. 4633, 1985 DOI: 10.1016/S0040-4039(00)98771-9

Health Hazard

Coniine is a highly toxic alkaloid. Thetoxic symptoms from ingestion are weakness,drowsiness, nausea, vomiting, muscle contraction, and labored breathing. A high dosecan cause convulsions, cyanosis, asphyxia,and death. Chronic ingestion of coniine produced adverse reproductive effects and spe cific developmental abnormalities in cattles.LD50 value, oral (mice): 100 mg/kg.

InChI:InChI=1/C8H17N/c1-2-5-8-6-3-4-7-9-8/h8-9H,2-7H2,1H3

Upstream product

• 110-89-4 piperidine 
• 187737-37-7 propene 
• 1604-01-9 6-propyl-2,3,4,5-tetrahydropyridine 
• 17618-94-9 2-(prop-1-en-1-yl)pyridine 
• 89656-44-0 2‐allylpiperidine 
• 89656-39-3 tert-Butyl-[1-(2-propyl-piperidin-1-yl)-meth-(E)-ylidene]-amine 
• 110-86-1 pyridine 
• 109-06-8 α-picoline 
• 522-33-8 Tripiperidin 
• 1257863-78-7 benzyl 2-propyl-3,4-dihydropyridine-1(2H)-carboxylate 
• 1108621-22-2 (Z)-N-hydroxyoct-5-en-1-amine 
• 90200-83-2 5-octen-1-ol 
• 1108621-23-3 C₁₁H₂₁NO 
• 1108621-30-2 1-(allyloxy)-2-propylpiperidine 

Downstream Products

• 220073-77-8 N-acetyl-(±)-coniine 
• 98195-27-8 1-benzyl-2-n-propylpiperidine 
• 51874-06-7 N-Benzoylconiine 
• 131248-79-8 2-propyl-piperidine-1-carbothioic acid anilide, (d-coniine)-N-carbothioic acid anilide 
• 65414-35-9 1-(2,4-dinitro-phenyl)-2-propyl-piperidine, N-(2.4-dinitro-phenyl)-d-coniine 
• 622-39-9 2-propylpyridine 
• 107-92-6 butyric acid 
• 56-12-2 4-amino-n-butyric acid 
• 5985-99-9 R(-)-coniine 
• 458-88-8 coniine 
• 1346681-79-5 benzyl (2R)-2-propylpiperidine-1-carboxylate 

Relevant academic research and scientific papers

Synthesis of heterocyclic enamine-zinc complexes as precursors of stereocontrolled substitution of nitrogen α-position

In the presence of ZnCl2, chiral protected amino-ketones and amino-aldehydes gave zinc enamino-complexes. Both enamine and iminium structures of these complexes were observed in 1H and 13C NMR spectra depending on the solvent. Introduction of either an allyl or a hydrogen substituent was performed using allylmagnesium chloride or NaBH4 in excess leading to various heterocycles. With the amino-ketones diastereoselectivity (de = 50) was observed respectively. Homoconiine and coniine precursors were prepared by this strategy.

AMMONIUM SALT, ELECTROLYTE FOR LITHIUM SECONDARY BATTERY, AND LITHIUM SECONDARY BATTERY USING THEM

PROBLEM TO BE SOLVED: To provide: ammonium salt with low viscosity; an electrolyte for a lithium secondary battery; and the lithium secondary battery. SOLUTION: This invention relates to an ammonium salt expressed by the following chemical formula (1). SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT

Proline catalyzed, one-pot three component Mannich reaction and sequential cyclization toward the synthesis of 2-substituted piperidine and pyrrolidine alkaloids

Abstract A very effective one-pot three component reaction of 4-bromobutanal or 5-bromopentanal, acetone, and p-anisidine catalyzed by proline is reported. A three component Mannich reaction followed by cyclization leading to the synthesis of 2-substituted pyrrolidine and piperidine derivatives through simultaneous formation of two C-N and one C-C bond is reported. The usefulness of the reaction is demonstrated by the synthesis of (±)coniine, (±)pelletrine, (±)sedridine, and (±)allosedridine.

A3-coupling reaction as a strategy towards the synthesis of alkaloids

A number of aldehydes, alkynols and benzylamines were submitted to A3-coupling reaction, under CuCl catalysis, giving strategically functionalized hydroxy-propargylamines. The procedure allows the use of alkyl as well as aryl aldehydes. Representative substrates were converted into five- and six-membered cyclic alkaloids by sequential one-pot N-debenzylation/triple bond reduction promoted by Pd, followed by a Mitsunobu-type cyclization.

Studies on difficult intramolecular hydroaminations in the context of four syntheses of alkaloid natural products

Examples of intramolecular alkene hydroaminations forming six-membered ring systems are rare, especially for systems in which the double bond is disubstituted. Such cyclizations have important synthetic relevance. Herein we report a systematic study of these cyclizations using recently developed Cope-type hydroamination methodologies. Difficult intramolecular alkene hydroaminations were used as key steps in syntheses of 2-epi-pumiliotoxin C, coniine, N-norreticuline and desbromoarborescidine A. This effort required the development of optimized hydroamination conditions to improve the efficiency of the cyclizations. Collectively, our results show that Cope-type cyclizations can be achieved on a variety of challenging substrates and proceed under similar conditions for both N-H and N-substituted hydroxylamines.

A concise and diastereoselective synthesis of piperidine and indolizidine alkaloids via aza-Prins cyclization

The synthesis of 2-substituted and 2,4-disubstituted piperidine alkaloids such as (±)-coniine, (±)-hydroxypipecolic acid, (±)-pipecolic acid, (±)-coniceine, and (±)-4-hydroxy-2- hydroxy-methyl piperidine have been accomplished in a highly diastereo-selective manner by employing aza-Prins cyclization as a key step to construct the piperidine core of these alkaloids. Georg Thieme Verlag Stuttgart · New York.

Hydroformylation of alkenylamines. Concise approaches toward piperidines, quinolizidines, and related alkaloids

Linear hydroformylation of N-protected allyl- or homoallylamines (cyclohydrocarbonylation: CHC), followed by a reductive amination constitute the two key steps toward convenient routes to aza-heterocycles.

High regioselectivity in electrochemical α-methoxylation of N-protected cyclic amines

N-Protecting groups of α-substituted cyclic amines strongly affected the regioselectivity in electrochemical methoxylation of these compounds. Namely, N-acyl derivatives were transformed into α′-methoxylated compounds, while N-cyano derivatives changed into α-methoxylated derivatives. Furthermore, Lewis acid catalyzed nucleophilic substitution of the α-methoxylated compounds protected with cyano group afforded α,α-disubstituted cyclic amines.

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.