Propranolol Hydrochloride → 1-[N-(1-Chloroethoxycarbonyl) isopropylamino]-3-(1-naphthyloxy)-2-propanol

Participants

Reaction Steps

A suspension of propanolol hydrochloride (3.0 g) in chloroform (100 ml) was mixed with proton sponge® (4.3 g) and cooled in an ice bath. 1-Chloroethyl chloroformate (1.5 g) was added dropwise to the reaction mixture. The suspension dissolved in about 5 minutes. The cooling bath was removed and the reaction mixture was stirred at room temperature for 1.5 hours. The chloroform solution was washed with water, 3N HCl and water successively. The organic layer was dried over Na2SO4 and evaporated to a thick oil weighing 3.6 g. NMR (CDCl3) δ1.25 (6H, d, J=7 Hz, CH(Me)2), 1.8 (3H, d, J=7 Hz, CH3CH), 3.3=3.6 (3H, m, ArOCH2 and CH(Me)2), 4.0-4.6 (3H, m, NCH2 and CHOH), 6.61 (1H, q, J=7 Hz, CH3CH) and 6.7-8.4 (7H, m, aromatic). IR (film) ν3450, 1715, 1583, 1270, 1248, 1108 cm-1.

Provenance & Evidence