1,2-Dichloroethane → Ammonia methanol

Participants

Reaction Steps

Combine (S)-2-methyl-10-(3-phenethyl-piperazin-1-yl)-4H-3-thia-1,4,9-triaza-benzo[f]azulene (0.5 g, 1.24 mmol) and 37% Formaldehyde solution (0.1 mL, 1.36 mmol)in 1,2-dichloroethane (25 mL). Stir for 10 minutes and add sodium triacetoxy borohydride (0.394, 1.86 mmol). Stir an additional 30 minutes and then pour solution onto saturated Sodium bicarbonate solution. Extract with methylene chloride to give 0.52 g of the crude product. Silica gel chromatography, eluting with methylene chloride: 2N NH3/methanol (100:3), gives 0.296 g of the title compound as the free base. The dihydrochloride salt precipitates in ethyl acetate as a yellow solid: mp 220° C.; mass spectrum (ion spray): m/z=418 (M+1); Analysis for C24H29Cl2N5S(0.5 H2O): calcd: C, 57.71; H, 6.05; N, 14.02; found: C, 57.81; H, 6.08; N, 13.81.

Provenance & Evidence