Réaction #61172

Équation de réaction

1-(5-fluoro-2-nitro-phenyl)-piperidine

EtOH DMF

NaCN

→

title compound

Rendement 27.0%

Dimethyl-(4-nitro-3-piperidin-1-yl-phenyl)-amine

Rendement 27.0%

Solvants

EtOAc

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water (2×50 mL)

Mode opératoire

To a solution of 1-(5-fluoro-2-nitro-phenyl)-piperidine (294 mg, 1.31 mmol, as prepared in the previous step) in 8 mL EtOH-DMF (v/v) was added NaCN (128 mg, 2.6 mmol). The reaction was heated to 130° C. in a sealed tube for 24 h. The reaction was diluted with EtOAc (50 mL) and washed with water (2×50 mL). Chromatography (50% EtOAc-hexane) of the crude product afforded 88 mg (27%) the title compound as well as 78 mg (24%) (1-(5-ethoxy-2-nitro-phenyl)-piperidine as yellow solids. Mass spectrum (ESI, m/z): Calcd. for C13H19N3O2, 250.1 (M+H), found 250.0.

Source