30727-18-5

Basic information

• Product Name: Ethyl 1-methylpipecolinate
• Synonyms: Methyl 1-Methyl Piperidine-2-carboxylate or Ethyl 1-Methyl-2-piperidinecarboxylate;Ethyl N-Methyl piperidine-2-carboxylate;ETHYL N-METHYLPIPECOLINATE;ETHYL 1-METHYL-2-PIPERIDINECARBOXYLATE;ETHYL 1-METHYLPIPECOLINATE;Ethyl 1-methylpiperidine-2-carboxylate~N-Methylpipecolinic acid ethyl ester;ethyl 1-methylpiperidine-2-carboxylate;ETHYL 1-METHYLPIPECOLINATE, 97+%
• CAS NO: 30727-18-5
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• EINECS: 250-311-2
• Mol File: 30727-18-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 92-96 °C11 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: clear colorless to brown liquid
• Density: 0.975 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.457mmHg at 25°C
• Refractive Index: n20/D 1.452(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.26±0.10(Predicted)
• CAS DataBase Reference: Ethyl 1-methylpipecolinate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 1-methylpipecolinate(30727-18-5)
• EPA Substance Registry System: Ethyl 1-methylpipecolinate(30727-18-5)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25
• WGK Germany: 3
• Hazardous Substances Data: 30727-18-5(Hazardous Substances Data)

Usage

Description

Ethyl 1-methylpipecolinate, also known as Ethyl Methylpiperidine-2-carboxylate, is an organic compound with the chemical properties of a clear colorless to brown liquid. It is a derivative of piperidine, a heterocyclic amine, and features an ester functional group. Ethyl 1-methylpipecolinate is known for its role in the synthesis of various chemical compounds and has potential applications in the pharmaceutical industry.

Uses

Used in Pharmaceutical Industry:
Ethyl 1-methylpipecolinate is used as a synthetic intermediate for the production of indole analogues, which serve as CB1 cannabinoid receptor agonists. These agonists have potential therapeutic applications in treating various conditions, such as pain, inflammation, and neurodegenerative disorders.
Additionally, Ethyl 1-methylpipecolinate is used as a synthetic intermediate in the synthesis of disubstituted thiadiazoles. These compounds have a wide range of applications, including pharmaceuticals, agrochemicals, and materials science, due to their diverse chemical properties and potential biological activities.

InChI:InChI=1/C7H13NO2/c1-10-7(9)6-4-2-3-5-8-6/h6,8H,2-5H2,1H3

Upstream product

• 50-00-0 formaldehyd 
• 15862-72-3 ethyl pipecolate 
• 34285-36-4 1-methyl-2-ethoxycarbonylpyridinium iodide 
• 2524-52-9 ethyl-2-picolinate 

Downstream Products

• 1360865-45-7 1-methyl-piperidine-2-carboxylic acid [1-(3,5-dichloro-2-hydroxy-phenyl)-methylidene]-hydrazide 
• 472-22-0 N,N-Dimethyl-piperidinium-2-carbonsaeure-betain 
• 626-67-5 N-methylcyclohexylamine 
• 74-85-1 ethene 
• 124-38-9 carbon dioxide 
• 7730-87-2 1-methylpiperidine-2-carboxylic acid 
• 204761-02-4 2-Benzotriazol-1-yl-1-(1-methyl-piperidin-2-yl)-2-p-tolyl-ethanone 
• 184033-70-3 2-Benzyl-2-ethoxycarbonyl-1-methylpiperidine 

Relevant articles and documents

Reductive alkylation of pyridinium salts. Part 1. Synthesis of di-, tetra- and hexa-hydropyridine esters

Reaction of 1-methyl-, 1-benzyl- and 1-benzoyl-4-ethoxycarbonylpyridinium salts 1 with zinc and benzyl bromide produce regioselectively the 4,4-disubstituted 1,4-dihydropyridines 3 (R = CH3, PhCH2, PhCO); only the latter is stable but all are reduced catalytically to piperidines 2 (R = CH3, PhCH2, PhCO). 1-Benzoyl-4-ethoxycarbonylpyridinium chloride with zinc and benzoyl chloride or ethyl bromoacetate gives respectively 4-benzoyl- 18 or 4-ethoxycarbonylmethyl-1-benzoyl-4-ethoxycarbonyl-1,4-dihydropyridine 17, but 1-methyl-4-ethoxycarbonylpyridinium iodide 1 (R = CH3, X = I) with benzoyl chloride gives 3-benzoyl-4-ethoxycarbonyl-1-methyl-1,2-dihydropyridine 21.The action of zinc and benzyl bromide on 1-methyl- and 1-benzyl-3-ethoxycarbonylpyridinium salts 5 gives, after catalytic hydrogenation, mixtures of 2- and 4-benzyl-5-ethoxycarbonyl-1,2,3,4-tetrahydropyridines 6 and 7 (R = CH3 or PhCH2) but similar treatment of 1-benzoyl-3-ethoxycarbonylpyridinium chloride 5 (R = PhCO, X = Cl) yields selectively the stable 4-benzyl-3-ethoxycarbonyl-1,4-dihydropyridine 9.Treatment of 1-methyl- or 1-benzoyl-3-ethoxycarbonylpyridinium salts 5 with zinc and benzoyl chloride gives a mixture of products. 1-Methyl-2-ethoxycarbonylpyridinium iodide 11 (R = CH3, X = I) reacts with zinc and benzyl bromide giving, after catalytic hydrogenation, 2-, 4- and 6-benzyl-2-ethoxycarbonyl-1-methylpiperidines 12, 13 and 14 (R = CH3) in the ratio 2:7:1, but 1-benzyl-2-ethoxycarbonylpyridinium bromide 11 (R = PhCH2, X = Br) gives only 1,4-dibenzyl-2-ethoxycarbonylpiperidine 13 (R = PhCH2).