Hydrogen Peroxide → HCID 11709404, compound

Participants

Reaction Steps

0.5 g of 4-dimethylaminomethyl-5-pyridin-3-yl-2,3,4,5-tetrahydro-benzo[b]thiepin-5-ol hydrochloride was dissolved in 2.5 ml of glacial acetic acid; about 0.23 ml of 35% hydrogen peroxide solution was added dropwise at room temperature, with stirring, and stirring was continued for 24 hours. The reaction mixture was covered with a layer of ethyl acetate, while cooling with ice, rendered alkaline with 32% sodium hydroxide solution and extracted twice with ethyl acetate; the combined organic phases were washed with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated in vacuo. 0.38 g of crude product was obtained and was chromatographed on silica gel with ethyl acetate/25% ammonia solution (v/v=98:2). 0.15 g of a mixed fraction and 0.13 g of dimethyl-(1-oxo-5-pyridin-3-yl-2,3-dihydro-1H-1λ4-benzo[b]thiepin-4-ylmethyl)-amine were obtained. The latter was dissolved in 6 ml of 2-acetone p.a. and converted into the corresponding hydrochloride with about 0.004 ml of water and about 0.043 ml of chlorotrimethylsilane, while cooling with ice; the hydrochloride was dried in vacuo (about 50 mbar) (yield 0.09 g of white solid).

Provenance & Evidence