Reaktion #10455

Reaktionsgleichung

nipecotic acid

benzyl bromide

potassium carbonate

→

title compound

Ausbeute 44.9%

1-Benzylpiperidine-3-carboxylic acid benzyl ester

Ausbeute 44.9%

Lösungsmittel

N,N-dimethylformamide

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe organic extract
2. 2
   Waschenis washed with 1.0 M hydrochloric acid, water and brine
3. 3
   Trocknendried over Na2SO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated in vacuo
6. 6
   SonstigeThe residue is purified by column chromatography (1:7 ethyl acetate/hexanes)

Vorschrift

To a solution added of nipecotic acid (8.0 g, 61.9 mmol) in N,N-dimethylformamide (80 mL) is benzyl bromide (31.8 g, 186 mmol) and potassium carbonate (42.8 g, 310 mmol). The mixture is heated at 70° C. for 18 hours and diluted with ethyl acetate and water. The organic extract is washed with 1.0 M hydrochloric acid, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue is purified by column chromatography (1:7 ethyl acetate/hexanes) to afford the title compound (8.6 g). 1H NMR (200 MHz, DMSO-d6): δ 7.27–7.42 (m, 10H), 5.07 (s, 2H), 3.45 (s, 2H), 2.88–2.49 (m, 3H), 2.32–1.32 (m, 6H).

Quelle