Sodium Hydroxide → HCID 86754290, compound

Participants

Reaction Steps

To a dry 100 ml round bottomed flask containing powdered molecular sieves 4A (1.5 g) was added 3,4-dihydro-1-(2-oxoethyl)-1H-2,1,3-benzothiadiazine-2,2-dioxide (0.8 g, 3.54 mmol) in methanol (30 ml)and 4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydropyridine (0.76 g) dissolved in methanol (10 ml). Borane-pyridine (1 ml) was added after 1 hour and the solution stirred overnight. 5 MHCl (10 ml) was added followed by 50% sodium hydroxide solution(5 ml) and water(5 ml). Solution was filtered through celite and ethyl acetate(3×50 ml) added. The organics were collected, washed with water, dried, filtered and the solvent removed in vacuo. Column chromatography through flash silica eluting with ethyl acetate/hexane gave product, 3,4-dihydro-(1-(2-[4-(6-fluoroindol-3-yl)-1,2,5,6-tetrahydro-1-pyridyl]-1-ethyl}-1H-2,1,3-benzothiadiazine-2,2-dioxide, m.p. 183-185° C.

Provenance & Evidence