Triethylamine → HCID 11407942, compound

Participants

Reaction Steps

To a solution of (1R)-2-[4-(2-Methoxy-phenyl)-piperazin-1-yl]-1-pyridin-2-ylmethyl-ethylamine (780 mg.; 2.4 mmol, from Example 13) in dichloromethane (30 mL) at 0° C. was added triethylamine (0.67 mL; 4.8 mmol) and a solution of cyclohexanecarbonyl chloride (0.33 mL; 2.45 mmol) in dichloromethane (5 mL). The reaction mixture was stirred while allowing to warm to ambient temperature over 1 hour. The mixture was washed with saturated NaHCO3 (15 mL), dried over MgSO4, filtered, and the solvent removed in vacuo. The crude residue was purified by flash chromatography on silica gel (2% methanol/chloroform) to afford the free base of the title compound as a white gummy foam (750 mg; 72%). Treatment with an equimolar amount of fumaric acid in ethanol yielded the fumarate salt as a white amorphous solid, m.p. 136–141° C.; MS (+) FAB [M+H]+ @ m/z 437, [M+Na]+ @ m/z 459; 1H NMR, 400 MHz, DMSO-d6. Analysis for C26H36N4O2. C4H4O4.2H2O Calculated: C, 61.21; H, 7.53; N, 9.52 Found: C, 61.79; H, 7.27; N, 9.31

Provenance & Evidence