3-Piperidinecarboxylic acid benzyl ester

3-Piperidinecarboxylic acid benzyl ester Property

Density 

1.092

storage temp. 

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

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Piperidinecarboxylic acid benzyl ester Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of benzyl 3-piperidinecarboxylate from benzyl 1-Boc-piperidine-3-carboxylate was as follows: benzyl 1-(tert-butoxycarbonyl)piperidinecarboxylate (7.11 g, 22.3 mmol) was dissolved in dichloromethane (20 mL) and trifluoroacetic acid (43 mL, 558 mmol) was added slowly. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the solvent was removed by concentration under reduced pressure and water was added to the residue, followed by dropwise addition of 1 mol/L aqueous sodium hydroxide to adjust the pH to basic. The aqueous phase was extracted with ethyl acetate and the organic layers were combined, washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the solvent was evaporated under reduced pressure to give benzyl 3-piperidinecarboxylate as a yellow oil (5.97 g, quantitative yield). The product was confirmed by 1H NMR (400 MHz, DMSO-d6): δ 1.45-1.70 (3H, m), 1.92-1.96 (1H, m), 2.59-2.69 (2H, m), 2.81 (1H, t, J = 9.8 Hz), 2.94-3.02 (1H, m), 3.21 (1H, dd, J = 12.6, 3.3 Hz), 5.10 (2H, d, J = 3.1 Hz), 7.27-7.38 (5H, m). Mass spectral analysis showed the molecular ion peak (EI+, m/z): 219 (M+).

References

[1] Patent: EP1780210, 2007, A1. Location in patent: Page/Page column 53
[2] Patent: WO2007/62007, 2007, A1. Location in patent: Page/Page column 87-88