Nitrogen → 4-Chloro-2-[4-(4-dimethylamino-benzyl)-piperazin-1-yl]-6-methyl-10,10-dioxo-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester

Participants

Reaction Steps

Titanium isopropoxide (0.33 mL, 1.09 mmol) was added to a solution of Example 104k (0.4 g, 0.91 mmol) and dimethylaminobenzaldehyde (0.136 g, 0.91 mmol) in dry methanol (10 mL). The reaction mixture was stirred at 50° C. in an atmosphere of N2 for 1.5 h. It was cooled, treated with sodium cyanoborohydride (0.054 g, 0.86 mmol) and stirred for 1.5 h. It was then treated with cold water and extracted with n-butanol. The organic layer was washed with water, brine, dried, concentrated and purified using flash chromatography (silica gel, MeOH/CHCl3) to obtain the title compound as a white solid. Yield: 0.275 g, (52.78%); 1H NMR (DMSO-d6): δ 2.7 (s, 3H, CH3), 3.00 (s, 6H, 2CH3), 3.20-3.25 (m, 4H, 2CH2), 3.55 (s, 4H, 2CH2), 3.95 (s, 3H, OCH3), 4.75 (s, 2H, CH2), 6.7-6.9 (m, 4H, Ar), 7.25 (s, 1H, Ar), 7.3 (s, 1H, Ar), 8.1 (s, 1H, Ar), 8.50 (s, 1H, Ar); MS: m/e (CI+) 570 (M+1).

Provenance & Evidence