Hydrochloric Acid → 4-Methanesulphonamidophenethyl mesylate

Participants

Reaction Steps

4-Aminophenethyl alcohol (2.74 g) was dissolved in dichloromethane (10 ml) and pyridine (5 ml) and then methanesulphonyl chloride (2×2.52 g) was added in 2 portions one hour apart, with stirring at 0°. After a further 2 hours, the mixture was acidified (to pH about 2) with 2N aqueous hydrochloric acid. The title compound (4.85 g) was filtered from the two-phase mixture. The organic layer plus a further dichloromethane extract of the aqueous layer yielded a further 0.95 g product after drying (sodium sulphate) and evaporation. The combined solids were washed with ether and recrystallized from ethyl acetate, yield of the title compound 4.13 g, m.p. 135°-7°.

Provenance & Evidence