Hexahydro-1,4-diazepine → HCID 131716943, compound

Participants

Reaction Steps

Add the product of step 1 (1.0 g, 2.9 mmol) in methylene chloride (10 mL) dropwise over 10 minutes to hexahydro-2H-1,4-diazepine (0.35 g) in methylene chloride (20 mL). Stir for 18 hours. Partition the reaction mixture between ethyl acetate (75 mL) and hydrochloric acid (75 mL, 1N). Separate, and adjust the pH of the aqueous layer to alkaline pH (phenolphthalein indicator) with aqueous sodium hydroxide (1N) forming a heavy precipitate. Extract the reaction mixture with methylene chloride (100 mL), wash with saturated aqueous sodium bicarbonate (100 mL), saturated aqueous sodium chloride (100 mL). Dry (MgSO4), filter and concentrate in vacuo to give the title compound free base (0.87 g) as a light yellow solid. Rf=0.52 (450:45:5 methylene chloride:methanol:acetic acid). Chromatograph the free base (120 mg) on a column of silica gel (300 g, 60 micron particle size) eluting with 1:9 methanol:methylene chloride to give a solid. Dissolve the solid in hydrochloric acid (10 mL) and concentrate to give the title compound (110 mg) as a white solid, as the semihydrate. Calculated for C18H21O2.5N2SBrCl: C, 47.76; H, 4.68; N, 6.18. Observed: C, 47.76; H, 4.39; N, 6.14.

Provenance & Evidence