Sodium Iodide → 2-Methylthio-10-[3-(4-beta-hydroxyethoxypiperidino)propyl]-phenothiazine hydrochloride

Participants

Reaction Steps

7 g (0.0469 mole) of sodium iodide were added to a solution of 15.1 g (0.0469 mole) of 2-methylthio-10-(3-chloropropyl)-phenothiazine in 250 ml of methyl ethyl ketone followed by the addition of 4.74 g (0.0469 mole) of triethylamine and then 6.8 g (0.0469 mole) of 2-(4-piperidyloxy)-ethanol. The mixture was refluxed for 20 hours and after cooling, the precipitate formed was removed by filtration. The filtrate was evaporated to dryness and the oil residue was dissolved in methylene chloride. The organic phase was washed with aqueous sodium bicarbonate, then with water, dried and concentrated. The resulting oil was dissolved in ethanol and an ether solution of hydrogen chloride was added thereto. The precipitate formed was recovered by vacuum filtration and twice crystallized from an ether-absolute ethanol mixture to obtain 9 g (41% yield) of 2-methylthio-10-[3-(4-β-hydroxyethoxypiperidino)propyl]-phenothiazine hydrochloride in the form of white crystals melting at 158°-160° C.

Provenance & Evidence