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

反応式

[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][CH2:6][CH2:7]2.[C:12]1([N:22]2[CH2:27][CH2:26][N:25]([CH2:28][CH2:29][CH2:30][OH:31])[CH2:24][CH2:23]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.[C:32](Cl)([Cl:34])=[O:33]>C1(C)C=CC=CC=1>[ClH:34].[C:12]1([N:22]2[CH2:23][CH2:24][N:25]([CH2:28][CH2:29][CH2:30][O:31][C:32](=[O:33])[NH:1][C:2]3[CH:11]=[CH:10][CH:9]=[C:8]4[C:3]=3[CH2:4][CH2:5][CH2:6][CH2:7]4)[CH2:26][CH2:27]2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

参加物

実験手順

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).