ChemicalBook CAS DataBase List Ethyl 4-piperidinecarboxylate

Ethyl 4-piperidinecarboxylate synthesis

6synthesis methods

Product Name:Ethyl 4-piperidinecarboxylate
CAS Number:1126-09-6
Molecular formula:C8H15NO2
Molecular Weight:157.21

Ethyl 4-piperidinecarboxylate belongs to carboxylic acid ester compound and can be used as pharmaceutical intermediates,it can be synthesized from ethyl 1-acetylpiperidine-4-carboxylate by chemical reaction.

498-94-2 Synthesis

498-94-2
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$5.00/10g

64-17-5 Synthesis

64-17-5
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$10.00/50g

1126-09-6
459 suppliers
$15.40/25g

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 0^οC 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 × CH_pip), 2.61 (td, J = 12.3, 2.7 Hz, 2H, 2 × CH_pip), 2.38 (tt, J = 11.3, 3.9 Hz, 1H, CH), 1.94 - 1.78 (m, 2H, 2 × CH_pip), 1.59 (adtd, J = 13.4, 11.4, 4.0 Hz, 2H, 2 × CH_pip), 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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