Methylamine → 3-(2,2-dioxido-1-phenyl-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)-N-methylpropan-1-amine hydrochloride

Participants

Reaction Conditions

Reaction Steps

3-(3-chloropropyl)-1-phenyl-3,4-dihydro-1H-2,1,3-benzothiadiazine 2,2-dioxide (0.030 g, 0.089 mmol) was dissolved in an 8 M solution of methylamine in tetrahydrofuran (5 mL), treated with KI (0.030 g, 0.18 mmol), and stirred in a capped vial at 50° C. for 20 hours. The reaction mixture was evaporated and the residue purified by flash chromatography (SiO2, 0-5% 7 M NH3-methanol/dichloromethane). The purified free-base was dissolved in ethyl ether (10 mL) and treated with hydrogen chloride (1.0 mL of a 2 M solution in ethyl ether), resulting in a white precipitate that was isolated by decantation and dried under vacuum to afford 3-(2,2-dioxido-1-phenyl-1,4-dihydro-3H-2,1,3-benzothiadiazin-3-yl)-N-methylpropan-1-amine hydrochloride (0.030 g, 92%) as a white solid:

Provenance & Evidence