Sodium Carbonate → 6-(4-morpholinyl)-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide

Participants

Reaction Steps

A solution of 4-acetyl-3,4-dihydro-2H-1,4-benzothiazin-6-amine 1,1-dioxide 2-bromo ethyl ether (1.276 g, 5.5 mmol) and sodium carbonate (1.06 g, 10 mmol) in MeOH (5 mL) was stirred at 150° C. for 1.5 h. After this time the reaction mixture was cooled to rt and LCMS shows intermediate 4-acetyl-6-morpholin-4-yl-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide. The compound was suspended in 3.5 mL of water and treated with KOH (1.82 g, 32.5 mmol) and the resulting mixture was stirred at 55° C. for 1 h. After this time the reaction was cooled and the resulting precipitate was filtered to give 6-morpholin-4-yl-3,4-dihydro-2H-1,4-benzothiazine 1,1-dioxide as white solid. Mass Spectrum (ESI) m/e=269 (M+1).

Provenance & Evidence