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【结 构 式】

【分子编号】30488

【品名】4-(4-isopropyl-1-piperazinyl)phenol; 1-Isopropyl-4-(4-hydroxyphenyl)piperazine

【CA登记号】

【 分 子 式 】C13H20N2O

【 分 子 量 】220.31468

【元素组成】C 70.87% H 9.15% N 12.72% O 7.26%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(A)

The condensation of 2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-(benzoyloxymethyl)-1,3-dioxolane (I) with triazole (II) by means of NaH in DMSO, followed by hydrolysis with NaOH in dioxane water gives 2-(2,4-dichlorophenyl)-2-(1H)-1,2,4-triazol-1-ylmethyl)-1,3-dioxolane-4-methanol (III), which is acylated with methanesulfonyl chloride in pyridine affording the corresponding 4-mesyloxymethyldioxolane (IV). Finally, this compound is condensed with 4-(4-isopropylpiperazin-1-yl)phenol (V) by means of NaH in hot DMSO. Compound (V) is obtained as follows: 4-(4-methoxyphenyl)piperazine (VI) is reductocondensed with acetone (A) by means of H2 over Pd/C giving 1-isopropyl-4-(4-methoxyphenyl)piperazine (VII), which is then demethylated with refluxing aqueous 48% HBr yielding (V)

1 Van Cutsem, J.; Heeres, J.; Hendrickx, R.; Antimycotic azoles. 6. Synthesis and antifungal properties of terconazole, a novel triazole ketal. J Med Chem 1983, 26, 4, 611-613.
2 Heeres, J.; Backx, L.J.J.; Mostmans, J.H. (Janssen Pharmaceutica NV); Novel 1-(1,3-dioxolan-2-ylmethyl)-1H-imidazoles. BE 0863382; FR 2378778; GB 1594859; JP 7895973; US 4144346; US 4223036 .
3 Serradell, M.N.; Castaner, J.; Fromtling, R.A.; Terconazole. Drugs Fut 1984, 9, 7, 529.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 30488 4-(4-isopropyl-1-piperazinyl)phenol; 1-Isopropyl-4-(4-hydroxyphenyl)piperazine C13H20N2O 详情 详情
(I) 30485 [(2S,4S)-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate; cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl]methyl benzoate C18H15BrCl2O4 详情 详情
(II) 13135 1H-1,2,4-Triazole; 1,2,4-Triazole 288-88-0 C2H3N3 详情 详情
(III) 30486 [(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methanol C13H13Cl2N3O3 详情 详情
(IV) 30487 1-[[(2S,4S)-2-(2,4-dichlorophenyl)-4-([[methyl(dimethylene)-lambda(6)-sulfanyl]oxy]methyl)-1,3-dioxolan-2-yl]methyl]-1H-1,2,4-triazole C16H19Cl2N3O3S 详情 详情
(V) 16312 1-(4-Methoxyphenyl)piperazine; Methyl 4-piperazinophenyl ether 38212-30-5 C11H16N2O 详情 详情
(VI) 23199 2-Propanone; Acetone; beta-ketopropane; chevron acetone;propan-2-one; Dimethyl formaldehyde; Dimethyl ketone; dimethylketal; Ketone propane; Methyl ketone; Propanone; Pyroacetic acid; Pyroacetic ether 67-64-1 C3H6O 详情 详情
(VII) 30489 1-isopropyl-4-(4-methoxyphenyl)piperazine; 4-(4-isopropyl-1-piperazinyl)phenyl methyl ether C14H22N2O 详情 详情
Extended Information