Dimethylformamide → 1-[3-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]-3-(2-hydroxy-1-hydroxymethylethyl)urea

Participants

Reaction Steps

1.02 g (2.0 mmol) of 4-nitrophenyl [3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)phenyl]carbamate hydrochloride (intermediate 1) were dissolved in 30 ml of abs. DMF and admixed at 0° C. with a solution of 200.5 mg (2.2 mmol) of 2-amino-1,3-propanediol in 25 ml of abs. DMF. The mixture was stirred at room temperature for 3 hours. After standing overnight, the solvent was removed in vacuo and the residue partitioned between ethyl acetate and saturated NaHCO3 solution. The organic phase was removed and the aqueous extracted twice more with ethyl acetate. The combined organic phases were washed with saturated NaCl solution, dried over Na2SO4 and concentrated. Chromatography of the crude product obtained in this way on silica gel (dichloromethane/methanol mixture) afforded 500 mg of the desired urea.

Provenance & Evidence