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

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

Uses

Used in Pharmaceutical Industry:
Ethyl 1-methylnipecotate is used as a reactant for the N-demethylation of tertiary amines, which is a crucial step in the synthesis of various pharmaceutical compounds. Its ability to facilitate this reaction makes it a valuable component in the development of new drugs.
Used in Chemical Synthesis:
In the field of chemical synthesis, Ethyl 1-methylnipecotate is used as a reactant for reverse cope elimination reactions. This reaction is essential for the synthesis of various complex organic molecules, making it a vital component in the creation of new chemical compounds.
Used in Regioselective Oxidation:
Ethyl 1-methylnipecotate is also used in regioselective oxidation processes, which are important for the synthesis of specific isomers with desired properties. Its ability to selectively oxidize certain functional groups makes it a valuable tool in the synthesis of various compounds.
Used in Chelating Agent Synthesis:
Ethyl 1-methylnipecotate is used as a reactant in the synthesis of chelating agents, which are essential for various applications, including the removal of metal ions from solutions and the stabilization of metal complexes.
Used in Sequential Michael-Michael-Dieckmann Cyclizations:
In the field of organic chemistry, Ethyl 1-methylnipecotate is used as a reactant in sequential Michael-Michael-Dieckmann cyclizations. This multi-step reaction is crucial for the synthesis of complex cyclic compounds, making it an important component in the development of new chemical structures.

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

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

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.).

REDUCTIVE ALKYLATION OF AMINES WITH ORTHOCARBOXYLIC ACID ESTERS

The present invention relates to a process for the N-alkylation of amines by reacting an amine with an orthocarboxylic acid ester and with hydrogen in the presence of a hydrogenation catalyst.

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

Disclosed are muscarinic agonist compounds including oxadiazole derivatives, compositions and preparations thereof. Also disclosed are methods of synthesizing such oxadiazole compounds. Further disclosed are methods for treating a subject with said muscarinic agonists or a pharmaceutically suitable form thereof to enhance cognitive function.

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.

1H-Indole-Pyridinecarboxamide and 1H-Indole-Piperidinecarboxamide Compounds

Compounds of formula (I): wherein: A represents a divalent radical: wherein: Z represents an oxygen atom or a sulphur atom,R6 represents a hydrogen atom, an alkyl, alkenyl, arylalkyl or polyhaloalkyl group or a substituted, linear or branched alkyl chain, represents a single bond or a double bond,R1, R2, R3 and R4 represent a hydrogen or halogen atom,an alkyl, alkoxy, hydroxy, cyano, nitro, polyhaloalkyl or optionally substituted amino group, or a linear or branched alkyl chain substituted by one or more groups,R5 represents a hydrogen atom or an alkyl, aminoalkyl or hydroxyalkyl group,X and Y represent a hydrogen atom or an alkyl group,Ra, Rb, Rc and Rd represent a hydrogen or halogen atom, an alkyl, hydroxy, alkoxy, cyano, nitro, polyhaloalkyl, optionally substituted amino group, or a substituted, linear or branched alkyl chain,Re represents a hydrogen atom or an alkyl, arylalkyl or alkenyl group or a substituted, linear or branched alkyl chain, their enantiomers, diastereoisomers, and N-oxides, and also addition salts thereof with a pharmaceutically acceptable acid or base.

Intriguing influence of the solvent on the regioselectivity of sulfoxide thermolysis in β-amino-α-sulfinyl esters

The sulfoxide thermolysis of the diastereoisomeric methyl (3R,4aS, 10aR)-6-methyl-3-methyl-3-(phenyl-sulfinyl)-1,2,3,4,4a,5,10,10a- octahydrobenzo[g]quinoline-3-carboxylates 3a and 3′b in toluene yields, by loss of benzenesulfenic acid, an almost 1:1 mixture of the vinylogous urethane 2b and the isomeric α-aminomethyl enoate 2a. When this elimination is performed in acetic acid, the enoate 2a is formed rather selectively. The same solvent effects on the regioselectivity of the elimination of benzenesulfenic acid are observed with a simple sulfoxide of ethyl piperidine-3-carboxylate (7).

Quinazoline derivatives and pharmaceutical compositions containing them

The invention relates to quinazoline derivatives of formula (1) wherein m is an integer from 1 to 2; R1represents hydrogen, hydroxy, halogeno, nitro, trifluoromethyl, cyano, C1-3alkyl, C1-3alkoxy, C1-3alkylthio, or —NR5R6(wherein R5and R6, which may be the same or different, each represents hydrogen or C1-3alkyl); R2represents hydrogen, hydroxy, halogeno, methoxy, amino or nitro; R3represents hydroxy, halogeno, C1-3alkyl, C1-3alkoxy, C1-3alkanoyloxy, trifluoromethyl, cyano, amino or nitro; X1represents —O—, —CH2—, —S—, —SO—, —SO2—, —NR7CO—, —CONR8—, —SO2NR9—, —NR10SO2— or —NR11— (wherein R7, R8, R9, R10and R11each independently represents hydrogen, C1-3alkyl or C1-3alkoxyC2-3alkyl); R4represents an optionally substituted 5 or 6 membered saturated carbocyclic or heterocyclic group or a group which is alkenyl, alkynyl or optionally substituted alkyl, which alkyl group may contain a heteroatom linking group, which alkenyl, alkynyl or alkyl group may carry a terminal optionally substituted group selected from alkyl and a 5 or 6 membered saturated carbocyclic or heterocyclic group, and salts thereof; processes for their preparation, pharmaceutical compositions containing a compound of formula (I) or a pharmaceutically acceptable salt thereof as active ingredient. The compounds of formula (I) and pharmaceutically acceptable salts thereof inhibit the effects of VEGF, a property of value in the treatment of a number of disease states including cancer and rheumatoid arthritis.

Soluble polymer bound cleavage reagents: A multipolymer strategy for the cleavage of tertiary amines from REM resin

(equation presented) Soluble polymer bound reagent 1 has been prepared to cleave tertiary amines from REM resin. Normally, amines cleaved from REM resin require extraction or chromatography to remove excess cleavage reagent and its byproducts. The solubility profile of non-crosslinked polystyrene (NCPS) based reagent 1 eliminates the need for such purification and allows for the direct isolation of a library of pure tertiary amines through simple filtration and concentration operations.