反応 #5947

反応方程式

1,4-benzodioxan-6-amine

phosgene

→

3,4-ethylenedioxyphenylisocyanate

溶媒

toluene

反応条件

後処理

1. 1
   温度was refluxed for 6 h
2. 2
   その他The solvent was removed under reduced pressure

実験手順

A mixture of 1,4-benzodioxan-6-amine (300 mg; 2.0 mmol) in toluene (20 ml) and phosgene (10 ml 20% in toluene; 19 mmol) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 3,4-ethylenedioxyphenylisocyanate. The crude product was added 3-[4-(4-chlorophenyl)-1-piperazinyl]propanol (500 mg; 2.0 mmol) in toluene (10 ml) and refluxed for 16 h. The reaction mixture was then concentrated and submitted to flash chromatography on silica gel 60 eluting with toluene graduated to toluene/ethyl acetate (1:1). The product was taken up in ethyl acetate, which was treated with hydrogen chloride in ether. Recrystallization from methanol/ether afforded 440 mg of the title compound. M.p. 243°-244° C. MS (70 eV): m/z 431 (31%, M+), 254 (34), 209 (100), 177 (75), 121 (31), 70 (38).

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