Hydrochloric Acid → 1-Cyclohexyl-4-[4-(2-methoxy-phenyl)-piperazin-1-YL]-2-phenyl-butan-1-one dihydrochloride

Participants

Reaction Steps

(+)-1-(2-methoxyphenyl)-4-[3-(cyclohexanecarbonyl)-3-(phenyl)butyl]piperazine (15.0 g, 34.5 mmol, prepared above) was diluted with methanol (40 mL). To this solution was added HCl (9.58 g of a 26.3% solution in methanol, 69.0 mmol). The mixture began to form gelatinous-looking crystals and set up solid within minutes. To this mixture was added with vigorous stirring, diethyl ether (100 mL). The white solid was collected by suction filtration and then dried under vacuum at 45° C. for two days to provide the title compound (13.4 g, 76%) as a white solid; mp(DSC)=195.58° C.; IR (CDCl3, cm−1) 2976, 2939, 1700, 1502, 1462, 1451, 1267, 1243, 1021; 1H NMR (300 MHz, DMSO) δ 7.40 (2H, m), 73.1 (3H, m) 7.03 (3H, M) 6.90 (1H, m) 3.78 (3H, s) 3.49 (4H, m) 3.16 (5H, m) 2.64 (1H, m) 2.40 (3H, m) 1.56 (3H, s) 1.46 (4H, m) 1.1; (5H, m) 0.86 (1H, m); 13C NMR (300 MHz, DMSO) δ 213.46, 151.84, 139.56, 138.12, 128.72, 127.37, 126.86, 124.29, 120.85, 118.71, 112.29, 55.48, 54.06, 52.20, 50.78, 50.57, 46.93, 45.14, 30.31, 30.16, 25.15, 24.91, 24.89, 19.15; HRMS calcd for C28H39N2O2 (MH+) 435.3012, found 435.3018. [α]25D=+76.53° (c=1, MeOH), ee 99.3% (Chiral HPLC).

Provenance & Evidence