Phosgene → 5-Isocyanato-1,2,3-trimethoxybenzene

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A mixture of 3,4,5-trimethoxyaniline (365 mg; 2.0 mmol) in toluene (20 ml) and phosgene (6 ml 20% in toluene; 12 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4,5-trimethoxyphenylisocyanate. The crude product was added 3-[4-(4-chloro-phenyl)-1-piperazinyl]propanol (800 mg; 3.1 mmol) in toluene (25 ml) and refluxed for 16 h. The solvent was evaporated and the residue taken up in ethanol, which was treated with hydrogen chloride in ether. Recrystallization from ethanol/ether afforded 620 mg of the title compound M.p. 173.5°-174.5° C.

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