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

Participants

Reaction Conditions

Reaction Steps

2-piperazin-1-yl-ethanol (0.227 g, 1.74 mmol) was added with stirring to a solution of Example 56k (0.5 g, 1.16 mmol) in DMF (10 mL) in an atmosphere of nitrogen. The reaction mixture was stirred at 110° C. for 6 h, concentrated, treated with chilled water and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, methanol/chloroform) to obtain the title compound as an off-white solid. Yield: 0.521 g, (85.69%); 1H NMR (DMSO-d6): δ 2.50 (s, 3H, CH3), 3.10 (t, 4H, 2CH2), 3.70 (t, 10H, 5CH2), 3.90 (s, 3H, OCH3), 4.40 (s, 2H, CH2), 5.20 (s, 2H, CH2), 6.10 (s, 1H, Ar), 6.80-6.85 (m, 2H, Ar), 8.10 (m, 2H, Ar); MS: m/e (ES+) 551 (M+).

Provenance & Evidence