Methyl isonipecotate Chemical Properties

Boiling point:

85-90 °C (lit.)

Density 

1.06 g/mL at 25 °C (lit.)

refractive index 

1.465

Flash point:

192°F

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Chloroform

form 

Liquid

pka

9.78±0.10(Predicted)

color 

Colorless to yellow

Water Solubility 

Slightly soluble in water.

CAS DataBase Reference

2971-79-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

RIDADR 

3267

WGK Germany 

3

HS Code 

29333990

MSDS

• Language:English Provider:4-Piperidinecarboxylic acid methyl ester

Methyl isonipecotate Usage And Synthesis

Chemical Properties

Colorless liquid

Uses

Methyl piperidine-4-carboxylate is a reactant for C-2 arylation of piperidines through directed transition metal-catalyzed sp3 C-H activation. It is used as a reactant for synthesis of antitubercular agents, aminopyrazine inhibitors, orally available naphthyridine protein kinase D inhibitors and a scalable catalyst from asymmetric hydrogenation of sterically demanding aryl enamide.

Uses

Methyl isonipecotate may be used for the synthesis of a series of potent non-urea soluble epoxide hydrolase (sEH) inhibitors via high throughput screens.

Uses

4-Piperidinecarboxylic acid methyl ester is a an ester derivative of 4-piperidinecarboxylic acid used as a reagent in the organic synthesis of neurochemicals, antibacterials and other biologically active compounds.

General Description

Methyl isonipecotate can be obtained by the reduction of methyl isonicotinate in methanol with ruthenium at 100-150°C.

Synthesis

The general procedure for the synthesis of methyl 4-piperidinecarboxylate from the compound (CAS: 1262670-73-4) is as follows: the substrate (1 eq.) was dissolved in a minimal amount of water (about 15 eq.) containing CAN (20 mol%). The reaction mixture was transferred to dichloromethane and magnetically stirred. Acetic acid (10 equivalents) was added to the solution, followed by stirring at room temperature for the time specified in Table 2. Upon completion of the reaction, the solvent was removed by evaporation under reduced pressure and post-treated as follows. Method A: The solid residue was washed twice with petroleum ether to remove the by-product triphenylmethanol. Subsequently, the residue was dissolved in methanol and filtered through a short diatomaceous earth pad. The solvent was removed by evaporation under reduced pressure to obtain the free amine. Method B: Water and acetic acid were removed from the reaction mixture under vacuum. The residue was dissolved in anhydrous dichloromethane, followed by the addition of triethylamine (2.5 eq.) and acetic anhydride or benzoyl chloride (1.5 eq.). After completion of the reaction, the solvent was removed by evaporation. The residue was extracted twice with ethyl acetate. The organic layers were combined, washed sequentially with water and brine and finally dried over Na2SO4. The solvent was removed by evaporation under reduced pressure and the resulting residue was purified by silica gel column chromatography to afford the acylated amine.

References

[1] Tetrahedron Letters, 2011, vol. 52, # 1, p. 34 - 37

Methyl isonipecotate(2971-79-1)Related Product Information

• Methylparaben
• Paraquat dichloride
• Basic Violet 1
• Methyl acrylate
• METSULFURON METHYL
• Methyl acetate
• RESMETHRIN
• Methyl salicylate
• Methyl benzoylformate
• Tribenuron methyl
• Methyl anthranilate
• Methanol
• Acetonitrile
• Methyl benzoate
• Methyl formate
• Isonipecotic acid
• Ethyl 4-piperidinecarboxylate
• Kresoxim-methyl