Hexahydro-1,4-diazepine → HCID 19826010, compound

Participants

Reaction Steps

Add the product of step 2 (0.5 g, 1.3 mmol) as a suspension in methylene chloride (10 mL) to hexahydro-2H-1,4-diazepine erazine (0.16 g) in methylene chloride (5 mL) at room temperature over 5 minutes. Stir the reaction mixture for 18 hours. Add aqueous sodium hydroxide (50 mL, 0.1N) to the reaction mixture, separate, and dry the organic layer (MgSO4), filter and concentrate to the title compound free base as a white solid. Chromatograph the solid on a column of silica gel (300 g) eluting with 5:95 methanol:methylene chloride. The solid is dissolved in aqueous hydrochloric acid (50 mL, 1N), concentrated, redissolved in water (25 mL) and lyophilized to give the title compound hydrate (200 mg, 31%) as a white solid. Rf=0.30 (1:9 methanol:methylene chloride). Calculated for C20H26O3N2SCl2Br: C, 49.04; H, 5.35; N, 5.72; S, 6.53. Observed: C, 48.62; H, 4.64; N, 5.70; S, 6.52.

Provenance & Evidence