Ethyl 4-piperidinecarboxylate synthesis
- Product Name:Ethyl 4-piperidinecarboxylate
- CAS Number:1126-09-6
- Molecular formula:C8H15NO2
- Molecular Weight:157.21
Yield:1126-09-6 94%
Reaction Conditions:
with thionyl chloride at 0; for 48 h;Reflux;
Steps:
Ethyl piperidine-4-carboxylate (22)
Isonipecotic acid (1.29g, 10.0 mmol) was dissolved in absolute ethanol (50 ml). The solution was cooled to 0οC and thionyl chloride (2.91 ml, 40.0 mmol) added dropwise. The solution was then stirred and refluxed for 48 h. The solvent was removed in vacuo yielding yellow oil, which was dissolved in EtOAc and washed with 10% NaOH. The organic layer was dried with anhydrous Na2SO4, filtered and concentrated in vacuo to afford a clear oil (1.48 g, 94%). 1H NMR (400 MHz, CDCl3) δ 4.12 (q, J = 7.1 Hz, 2H, OCH2CH3), 3.07 (dt, J = 12.6, 3.6 Hz, 2H, 2 × CHpip), 2.61 (td, J = 12.3, 2.7 Hz, 2H, 2 × CHpip), 2.38 (tt, J = 11.3, 3.9 Hz, 1H, CH), 1.94 - 1.78 (m, 2H, 2 × CHpip), 1.59 (adtd, J = 13.4, 11.4, 4.0 Hz, 2H, 2 × CHpip), 1.24 (t, J = 7.1 Hz, 3H, OCH2CH3). Mass Spectrum (ESI): m/z 158.2 [M+H]+.
References:
Nguyen, William;Howard, Brittany L.;Jenkins, David P.;Wulff, Heike;Thompson, Philip E.;Manallack, David T. [Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,# 23,p. 7106 - 7109] Location in patent:supporting information
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![4-Piperidinecarboxylic acid, 1-[2-(2,4-dinitrophenoxy)-1-oxidodiazenyl]-, ethyl ester](/CAS/20210111/GIF/1083159-13-0.gif)
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