Reaktion #166393

Reaktionsgleichung

acetonitrile

2-chloro-5-(chloromethyl)pyridine

piperazinone

potassium carbonate

→

compound 356

Ausbeute 34.3%

4-((6-Chloropyridin-3-yl)methyl)piperazin-2-one

Ausbeute 34.3%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationUpon workup, the mixture was filtered through a layer of celite and the cake
2. 2
   Waschenwas washed with ethyl acetate
3. 3
   EinengenThe filtrate was concentrated in vacuo

Vorschrift

A mixture of 2-chloro-5-(chloromethyl)pyridine (1.4 g, 8.4 mmol), piperazinone (0.84 g, 8.4 mmol), and potassium carbonate (1.0 mL, 17 mmol) in a mixed solvent consisting of acetonitrile (40 mL) and THF (20 mL) was stirred at room temperature for 3.5 days. Upon workup, the mixture was filtered through a layer of celite and the cake was washed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was subjected to combi-flash column chromatography (methanol/DCM) to give compound 356 (0.65 g, 34% yield) as an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.35 (1 H, d, J=2.0 Hz), 7.81 (1 H, dd, J=8.1, 2.4 Hz), 7.76 (1 H, br. s.), 7.49 (1 H, d, J=8.3 Hz), 3.57 (2 H, s), 3.10-3.16 (2 H, m), 2.93 (2 H, s), 2.52-2.56 (2H, m). LCMS-ESI (POS), M/Z, M+1: Found 226.0.

Quelle