1-Bromo-3-chloropropane → 2-(3-Chloropropyl)-6,7-dimethoxy-1,2,3,4-tetrahydro-isoquinolin-1-one

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Reaction Conditions

Reaction Steps

2.1 gm (44 millimols) of sodium hydride were added to a solution of 8.0 gm (41 millimols) of 6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one in 100 ml of dimethyl formamide, and the mixture was heated at 80° C. for 30 minutes. Then, 20 ml of 1-bromo-3-chloro-propane were added dropwise, and the mixture was heated at 100° C. for 3 hours. The solvent was then removed in vacuo, the solid residue was digested in water, and the aqueous mixture was extracted with chloroform several times. The combined organic extracts were dried over sodium sulfate and evaporated to dryness, and the evaporation residue was purified by chromatography on silica gel (chloroform/methanol = 150/l), yielding 3.2 gm of 1-(6,7-dimethoxy-3,4-dihydro-2H-isoquinolin-1-one-2-yl)-3-chloro-propane as a viscous oil having an Rf -value of 0.8 (ethyl acetate).

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