Hydrochloric Acid → N-{3-[7-Amino-8-(4-chlorobenzyl)-5,6,7,8-tetrahydronaphthalen-2-yl]propyl}propane-1-sulfonamide hydrochloride

Participants

Reaction Steps

tert-Butyl [1-(4-chlorobenzyl)-7-{3-[(propylsulfonyl)amino]propyl}-1,2,3,4-tetrahydronaphthalen-2-yl]carbamate (150 mg, 0.281 mmol) was dissolved in dichloromethane (3 mL) and a solution of hydrochloric acid (0.5 mL, 5 M in isopropanol) was added. After stirring at room temperature for 2 hours the solvent was removed in vacuo. Water was added (15 mL) and the pH was adjusted to 9 with aqueous saturated sodium bicarbonate and the mixture was extracted with dichloromethane (3×15 mL). The combined organic extracts were dried and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). The product was dissolved in dichloromethane (2 mL) and a solution of hydrochloric acid in ethanol (1.25 M) was added. The solvent was removed in vacuo. Yield: 31.4 mg (0.187 mmol, 36%).

Provenance & Evidence