Hydrochloric Acid → Sarizotan Hydrochloride

Participants

Reaction Steps

20.3 g of (R)-2-aminomethylchroman hydrochloride are introduced into 150 ml of ethanol, and 36.8 g of a 20% solution of sodium ethoxide in ethanol are added dropwise with stirring. 20.5 g of 5-(4-fluorophenyl)pyridine-3-carbaldehyde are added to the suspension at 35° C., and the mixture is stirred for a further 3 hours. After addition of 4.2 g of sodium borohydride, the mixture is stirred for a further 4 hours, and 62 ml of water are then added dropwise at room temperature. The pH of the reaction mixture is then adjusted to pH 4 using 37% hydrochloric acid over the course of one hour. The crystals are filtered off, rinsed with ethanol and dried under reduced pressure, giving 27.2 g of (R)-(−)-2-[5-(4-fluorophenyl)-3-pyridylmethylaminomethyl]chroman hydrochloride (69% yield).

Provenance & Evidence