Hydrochloric Acid → 4-Chloro-2-[4-(2-hydroxy-ethyl)-piperazine-1-yl]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

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Reaction Conditions

Reaction Steps

Ethanol amine (0.25 mL, 4.17 mmol) was added to a solution of Example 102j (0.5 g, 1.04 mmol) in methanol (5 mL) in an atmosphere of nitrogen and sealed in a pressure reactor vessel at 120° C. for 4 h. It was brought to room temperature, treated with, chilled water, dilute HCl to neutral pH and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated, treated with methanolic HCl solution, and refluxed at 70° C. for 3 h. The reaction mixture was concentrated, treated with aqueous sodium bicarbonate solution to neutral pH and extracted with ethyl acetate. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, 5% methanol/chloroform) to obtain the title compound. Yield: 0.337 g, (67.13%); 1H NMR (DMSO-d6): δ 2.70 (s, 3H, CH3), 3.05-3.15 (m, 4H, 2CH2), 3.40-3.45 (m, 8H, 4CH2), 3.70 (s, 1H, OH), 3.90 (s, 3H, OCH3), 5.20 (s, 2H, CH2), 7.10 (s, 1H, Ar), 7.20 (s, 1H, Ar), 8.15 (s, 1H, Ar), 8.20 (s, 1H, Ar); MS: m/e (EI+) 481 (M+1).

Provenance & Evidence