Ethyl 1-methylnipecotate Chemical Properties

Boiling point:

88-89 °C/11 mmHg (lit.)

Density 

0.954 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.451(lit.)

Flash point:

155 °F

storage temp. 

Sealed in dry,Room Temperature

form 

clear liquid

pka

8.56±0.10(Predicted)

color 

Colorless to Almost colorless

BRN 

123259

CAS DataBase Reference

5166-67-6(CAS DataBase Reference)

NIST Chemistry Reference

Ethyl 1-methylnipecotate(5166-67-6)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39-37/39

WGK Germany 

3

F 

9-23

Hazard Note 

Irritant

HS Code 

29333990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS

Ethyl 1-methylnipecotate Usage And Synthesis

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.

Synthesis

The general procedure for the synthesis of ethyl 1-methyl-3-piperidinecarboxylate from triethyl orthoformate and ethyl crotonate is as follows: in an autoclave, a 1 molar concentration of catalyst based on the molar amount of amine is added, and after displacing the air in the autoclave with argon, 0.1 moles of amine and 0.11-0.3 moles of o-carboxylic acid ester dissolved in a 10 ml solution in methanol (or ethanol) are added, as well as 0.5 ml of 0.2 M anhydrous p-toluene benzenesulfonic acid solution in methanol (or ethanol). The reaction mixture was heated to 120°C and charged with hydrogen gas to a pressure of 40 bar. The reaction mixture was stirred continuously at a constant pressure until the absorption of hydrogen ceased (reaction time of about 0.2-6 hours). After completion of the reaction, the catalyst was removed by filtration and the filtrate was distilled to purify the target product.

References

[1] Patent: WO2017/133913, 2017, A1. Location in patent: Page/Page column 9; 14

Ethyl 1-methylnipecotate(5166-67-6)Related Product Information

• Ethylparaben
• Triethyl orthoformate
• 2,2,6,6-Tetramethyl-4-piperidinol
• Urethane
• Ethyl formate
• Nipecotic acid
• Ethyl cyanoacetate
• Ethyl acetate
• Bensulfuron methyl
• Methyl acrylate
• Ethyl acrylate
• Trinexapac-ethyl
• ISOXADIFEN-ETHYL
• Methyl acetate
• Methylparaben
• Triacetonediamine
• Thiophanate-methyl
• Kresoxim-methyl