반응 #5955

반응 방정식

3-[4-(1-naphthyl)-1-piperazinyl]propanol

5-amino-1,2,3,4-tetrahydronaphthalene

phosgene

→

title compound

4-(1-Naphthyl)-1-[3-(1,2,3,4-tetrahydro-5-naphthylcarbamoyloxy)propyl]piperazine, hydrochloride

용매

toluene

toluene

반응 조건

후처리

1. 1
   온도was refluxed for 6 h
2. 2
   기타The solvent was removed under reduced pressure
3. 3
   기타to give crude 1,2,3,4-tetrahydronaphthyl -5-isocyanate
4. 4
   온도refluxed for 6 h
5. 5
   농축The reaction mixture was then concentrated
6. 6
   workup.ADDITIONwhich was treated with hydrogen chloride in ether

실험 절차

A mixture of 5-amino-1,2,3,4-tetrahydronaphthalene (300 mg; 2.0 mmol) in toluene (10 ml) and phosgene (10 ml 20% in toluene) was refluxed for 6 h. The solvent was removed under reduced pressure to give crude 1,2,3,4-tetrahydronaphthyl -5-isocyanate. To the crude product was added 3-[4-(1-naphthyl)-1-piperazinyl]propanol (240 mg; 2.0 mmol) in toluene (60 ml) and refluxed for 6 h. The reaction mixture was then concentrated and submitted to flash chromatography on silica gel 60 eluting with dichloromethane graduated to dichloromethane/ethyl acetate (1:1). The product was taken up in ethanol, which was treated with hydrogen chloride in ether to give 340 mg of the title compound. M.p. 227°-229° C. MS (70 eV): m/z 443 (M+,46), 270 (39), 225 (100), 173 (45), 145 (31), 127 (21), 114 (31), 70 (80).

출처