Toluene → HCID 178471786, compound

Participants

Reaction Steps

A mixture of 3-fluoropyridine-2-carbaldehyde (122.7 mg, 0.981 mmol), ethyl{trans-4-[(ethylamino)methyl]cyclohexyl}acetate (202.7 mg, 0.892 mmol), potassium carbonate (369.7 mg, 2.67 mmol) and dry toluene (13 mL) was heated at reflux under N2 overnight. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (3×20 mL). The combined extracts were dried (Na2SO4) and concentrated in vacuo to give the crude product. This was purified by flash chromatography (Si, 12×160 mm, 0-50% EtOAc in hexanes gradient) to afford ethyl (trans-4-{[ethyl(2-formylpyridin-3-yl)amino]methyl}cyclohexyl)acetate as a yellow oil. Rf=0.79 (50% EtOAc/hexanes). LCMS calc.=333.2; found=333.3 (M+1)+. 1H NMR (600 MHz, CDCl3): δ 10.13 (s, 1 H); 8.29 (d, J=4.1 Hz, 1 H); 7.41 (d, J=8.5 Hz, 1 H); 7.29 (dd, J=4.1, 8.4 Hz, 1 H); 4.08 (q, J=7.1 Hz, 2 H); 3.26 (q, J=7.0 Hz, 2 H); 3.05 (d, J=7.1 Hz, 2 H); 2.12 (d, J=6.9 Hz, 2 H); 1.71 (m, 4 H); 1.66 (m, 1 H); 1.41 (m, 1 H); 1.22-1.20 (t, J=7.1 Hz, 3 H); 1.06 (t, J=7.1 Hz, 3 H); 0.91-0.82 (m, 4 H).

Provenance & Evidence