Ethyl 1-benzylpiperidine-4-carboxylate Chemical Properties

Boiling point:

122°C (0.5 mmHg)

Density 

1.037 g/mL at 25 °C

refractive index 

1.5120-1.5160

Flash point:

>110℃

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Chloroform (Slightly), Hexanes (Slightly), Methanol (Slightly)

form 

clear liquid

pka

7.93±0.10(Predicted)

color 

Colorless to Light red

InChI

InChI=1S/C15H21NO2/c1-2-18-15(17)14-8-10-16(11-9-14)12-13-6-4-3-5-7-13/h3-7,14H,2,8-12H2,1H3

InChIKey

ASQCOPJFYLJCGD-UHFFFAOYSA-N

SMILES

N1(CC2=CC=CC=C2)CCC(C(OCC)=O)CC1

CAS DataBase Reference

24228-40-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,T

Risk Statements 

36/37/38-25

Safety Statements 

24/25-45

RIDADR 

UN 2810 6.1 / PGIII

Hazard Note 

Irritant

HS Code 

29333990

Ethyl 1-benzylpiperidine-4-carboxylate Usage And Synthesis

Uses

Ethyl 1-benzyl-4-piperidinecarboxylate and its derivatives are important pharmaceutical intermediates with high biological activity. Ethyl 1-benzyl-4-piperidinecarboxylate can be used to synthesize anti-inflammatory drug trypsin inhibitors, antagonizing inflammatory mediators at the receptor level. It can also be used to synthesize antitumor drugs such as matrix metalloproteinase inhibitors and farnesyltransferase inhibitors. In summary, ethyl 1-benzyl-4-piperidinecarboxylate and its derivatives possess excellent biological activity and can be used not only to synthesize GABA uptake inhibitors and antitumor drugs, but also to synthesize growth hormone secretagogues, anti-inflammatory and analgesic drugs, cardiovascular drugs, nootropic drugs, antiviral drugs, and bone disease drugs.

Synthesis

Ethyl isonipecotate (50 g, 0.31 mol) was dissolved in toluene (150 mL) in a round bottom flask, charged with potassium carbonate (60 g, 0.43 mol) and stirred for 15 min. Benzyl chloride (42 g, 0.31 mol) was charged and the reaction mass was refluxed for 4 h at 100 °C. Upon completion of the reaction as marked by TLC (hexane:ethyl acetate; 2:1), the reaction mass was cooled to room temperature and quenched with water (100 mL), stirred and the organic phase was separated. The aqueous phase was again extracted with toluene (100 mL). Combined organic phase was washed twice with saturated brine solution (50 mL). Remove toluene in vacuo to obtain Ethyl N-benzylpiperidine-4-carboxylate ( 6.97 g, 91 %) as a yellow liquid.

Chemical Properties

Colourless Oil

References

[1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 22, p. 6938 - 6942,5
[2] Journal of medicinal chemistry, 1980, vol. 23, # 8, p. 848 - 851
[3] Patent: WO2010/12611, 2010, A1. Location in patent: Page/Page column 28
[4] Journal of Medicinal Chemistry, 1996, vol. 39, # 3, p. 749 - 756
[5] Organic Preparations and Procedures International, 1994, vol. 26, # 3, p. 421 - 428

Ethyl 1-benzylpiperidine-4-carboxylate(24228-40-8)Related Product Information

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