5166-67-6

Basic information

• Product Name: Ethyl 1-methylnipecotate
• Synonyms: ETHYL 1-METHYLPIPERIDINE-3-CARBOXYLATE;ETHYL 1-METHYLNIPECOTATE;ETHYL 1-METHYL-3-PIPERIDINE-CARBOXYLATE;Ethyl 1-methylpiperidine-3-carboxylate 97%;Ethyl 1-methylnipecotate, 98+%;1-Methyl-3-piperidinecarboxylic acid ethyl ester;Ethyl N-Methyl piperidine-3-carboxylate or Ethyl 1-Methylnipecotate;Ethyl N-Methylpiperidine-3-carboxylate
• CAS NO: 5166-67-6
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• EINECS: 225-951-0
• Product Categories: Heterocyclic Compounds
• Mol File: 5166-67-6.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 88-89 °C11 mm Hg(lit.)
• Flash Point: 155 °F
• Appearance: Clear colorless to pale yellow liquid
• Density: 0.954 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.186mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 8.56±0.10(Predicted)
• BRN: 123259
• CAS DataBase Reference: Ethyl 1-methylnipecotate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 1-methylnipecotate(5166-67-6)
• EPA Substance Registry System: Ethyl 1-methylnipecotate(5166-67-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• WGK Germany: 3
• F: 9-23
• Hazardous Substances Data: 5166-67-6(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless to pale yellow liquid

Uses

Reactant for: N-demethylation of tertiary amines Reverse cope elimination reactions Regioselective oxidation Synthesis of chelating agents Sequential Michael-Michael-Dieckmann cyclizations

General Description

Enantiomeric discrimination has been investigated in 1H and 13C NMR spectra of ethyl 1-methyl-3-piperidinecarboxylate in the presence of (-)-(18-crown-6)-2,3,11,12-tetracarboxylic acid.

InChI:InChI=1/C9H17NO2/c1-3-12-9(11)8-5-4-6-10(2)7-8/h8H,3-7H2,1-2H3/p+1/t8-/m0/s1

Upstream product

• 614-18-6 3-pyridinecarboxylic acid ethyl ester 
• 108320-80-5 3-ethoxycarbonyl-1-methyl-pyridinium; bromide 
• 56338-90-0 3-ethoxycarbonyl-1-methylpyridinium chloride 
• 71962-74-8 Ethyl nipecotate 
• 74-88-4 methyl iodide 
• 50-00-0 formaldehyd 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 470700-27-7 ethyl 1-methyl-3-(phenylsulfanyl)piperidine-3-carboxylate 
• 4842-86-8 ethyl piperidine-3-carboxylate hydrochloride 
• 136081-13-5 ethyl 1-methyl-3-(2'-fluoro)-benzyl-nipecotate 
• 205194-11-2 (R)-3-hydroxymethyl-1-methylpiperidine 
• 111-84-2 nonane 
• 470700-28-8 ethyl 1-methyl-3-(phenylsulfinyl)piperidine-3-carboxylate 
• 28125-84-0 Homoarecoline 
• 626-67-5 N-methylcyclohexylamine 
• 74-85-1 ethene 
• 124-38-9 carbon dioxide 
• 114193-37-2 N-methyl-N-(3-phenyl-5-isoxazolyl)-1-methylnipecotamide 

Relevant articles and documents

Reductive Alkylation of Amines with Carboxylic Ortho Esters

We have demonstrated for the first time that carboxylic ortho esters could be used as an alkylating agent in the reductive alkylation of amines. A variety of amines, including amino acid esters, were alkylated affording mono-alkylated products with high selectivity in practical to high yields using standard heterogeneous catalysts. By applying acyclic ortho esters alkylation was completed at room temperature. (Figure presented.).

COGNITION ENHANCING COMPOUNDS AND COMPOSITIONS, METHODS OF MAKING, AND METHODS OF TREATING

The invention relates generally to muscarinic agonists, which are useful for stimulating muscarine, receptors and treating cognitive disorders. Included among the muscarinic agonists disclosed herein are oxadiazole derivatives compositions, and preparations thereof. Methods of synthesizing oxadiazole compounds also are provided. This disclosure also relates in part to compositions for enhancing cognitive function in subjects such as humans. The compositions comprising a muscarinic agonist or a pharma.ceutically suitable form thereof. This disclosure relates in part to methods of treating animals such as humans by administering such compositions.

COMPOUNDS AND COMPOSITIONS FOR COGNITION-ENHANCEMENT, METHODS OF MAKING, AND METHODS OF TREATING

Muscarinic agonists, which are useful for stimulating muscarinic receptors and treating cognitive disorders, are provided. Methods of synthesizing such agonists also are provided. Also provided are compositions for enhancing cognitive function in subjects such as humans, the compositions comprising a muscarinic agonist or a pharmaceutically suitable form thereof. Also provided are methods of treating animals such as humans by administering such compositions.