Reaction #46409

Reaction equation

CH2Cl2 methanol

11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione

pentyl isocyanate

→

desired product

Yield 28.0%

1-{2-[2-(dimethylamino)ethyl]-1,3-dioxo-2,3-dihydro-1H-dibenzo[de,h]isoquinolin-11-yl}-3-pentylurea

Yield 28.0%

Solvents

acetonitrile

acetonitrile

Conditions

Workup

1. 1
   OtherThe solvent was then evaporated under reduced pressure

Procedure

A solution of 100 mg (0.30 mmole) of 11-amino-2-[2-(dimethylamino)ethyl]-1H-dibenzo[de,h]isoquinoline-1,3(2H)-dione (obtained in example 3) in 4 mL of acetonitrile was stirred at 20° C. 156 μL (4 molar equivalents) of pentyl isocyanate in 3 mL acetonitrile were added. The mixture was magnetically stirred at 20° C. during 18 hours. The solvent was then evaporated under reduced pressure and the residue was submitted to a flash chromatography on silica (eluent: CH2Cl2/methanol in a 95:5 ratio) to provide 37 mg (yield: 28%) of the desired product (formula below) as an orange powder

Source