2-(PIPERIDIN-4-YL)-ACETIC ACID ETHYL ESTER Chemical Properties

Melting point:

192 °C (decomp)

Boiling point:

67°C/0.22mm

Density 

0.969±0.06 g/cm3(Predicted)

storage temp. 

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

form 

liquid

pka

10.41±0.10(Predicted)

CAS DataBase Reference

59184-90-6(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

2-(PIPERIDIN-4-YL)-ACETIC ACID ETHYL ESTER Usage And Synthesis

Uses

Piperidine derivatives have significant research value in the pharmaceutical field as drug intermediates. 4-Piperidine acetate methyl ester is also an important piperidine derivative drug intermediate, mainly used in the synthesis of drugs for various neurological diseases, such as convulsions, anti-epileptic drugs, and sedatives.

Synthesis

General procedure for the synthesis of ethyl 4-piperidineacetate from ethyl 2-(1-benzylpiperidin-4-ylidene)acetate: palladium/carbon catalyst (3.94 g) was added to a solution of 2-(1-benzylpiperidin-4-ylidene)ethyl acetate (24 g, 93 mmol) in ethyl acetate (300 mL). The reaction mixture was placed in an H-cubic hydrogenation reactor and the reaction conditions were set at 55 °C and 55 psi for 16 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to afford ethyl 4-piperidineacetate as a colorless oil (15 g, 90% yield). The product was characterized by 1H NMR (400 MHz, CDCl3) with chemical shifts δ: 4.10 (m, 2H), 3.03 (d, J = 16.4 Hz, 2H), 2.59 (t, J = 16.4 Hz, 2H), 2.19 (d, J = 9.6 Hz, 2H), 1.87 (m, 1H), 1.67 (d, J = 17.2 Hz, 2H ), 1.23 (t, J = 9.6Hz, 3H), 1.10 (m, 2H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 11, p. 3065 - 3067
[2] Patent: WO2013/107336, 2013, A1. Location in patent: Page/Page column 17; 18
[3] Patent: US2015/80380, 2015, A1. Location in patent: Paragraph 0081; 0137; 0138; 0139
[4] Synthetic Communications, 2003, vol. 33, # 13, p. 2329 - 2338

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