Potassium Carbonate → HCID 11178774, compound

Participants

Reaction Steps

To a solution of (2R)-1-[4-(2-methoxyphenyl)piperazin-1-yl]-N-methyl-3-pyridin-2-ylpropan-2-amine (90 mg.; 0.26 mmol, from Example 17) in dichloromethane (3 mL) at 0° C. was added a solution of potassium carbonate (180 mg.; 1.3 mmol) in water (0.5 mL), followed by a solution of 1-methyl-1-cyclohexanecarbonyl chloride (41 mg.; 0.26 mmol) in dichloromethane (0.5 mL). The reaction mixture was stirred while allowing to warm to ambient temperature over 1 hour, diluted with dichloromethane (5 mL), and the layers allowed to separate. The organic layer was dried over MgSO4, filtered, and the solvent removed in vacuo. The crude residue was purified by flash chromatography on silica gel (10% methanol/ethyl acetate) to yield the free base of the title compound as a clear oil (68 mg.; 56%). Treatment with an equimolar amount of fumaric acid in acetonitrile afforded the fumarate salt as a white crystalline solid, m.p. 145–146° C.; MS (+) ESI [M+H]+ @ m/z 465; 1H NMR, 400 MHz, DMSO-d6. Analysis for C28H40N4O2.C4H4O4 Calculated: C, 66.18; H, 7.64; N, 9.65 Found: C, 65.95; H, 7.41; N, 9.54

Provenance & Evidence