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【结 构 式】 
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【分子编号】36165 【品名】4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-amine; 4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-ylamine 【CA登记号】 |
【 分 子 式 】C17H24N2O4 【 分 子 量 】320.38864 【元素组成】C 63.73% H 7.55% N 8.74% O 19.97% |
合成路线1
该中间体在本合成路线中的序号：(IV)The condensation of 5-acetamido-4,7-dimethoxy-6-hydroxybenzofuran (I) with N-(2-chloroethyl)piperidine (II) by means of K2CO3 in refluxing acetone gives 5-acetamido-4,7-dimethoxy-6-[2-(N-piperidino)ethoxy]benzofuran (III), which is hydrolyzed with refluxing 2N HCl yielding 5-amino-4,7-dimethoxy-6-[2-(N-piperidino)ethoxy]benzofuran (IV). Finally, this compound is treated with methyl isocyanate (V) in hot toluene.
| 【1】 Bourgery, G.; Lacour, A.; Pourrias, B.; Bregeon, G.C. (Laboratoires Delalande); Novel aminoalkoxybenzofurans, their process of preparation and their therapeutic use. FR 2358143 . |
| 【2】 Serradell, M.N.; Castaner, J.; Blancafort, P.; Thorpe, P.J.; Murocainide. Drugs Fut 1983, 8, 8, 687. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 34144 | N-(6-hydroxy-4,7-dimethoxy-1-benzofuran-5-yl)acetamide | C12H13NO5 | 详情 | 详情 | |
| (II) | 10117 | 1-(2-Chloroethyl)piperidine; N-(2-Chloroethyl)piperidine | 1932-03-2 | C7H14ClN | 详情 | 详情 |
| (III) | 36164 | N-[4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-yl]acetamide | C19H26N2O5 | 详情 | 详情 | |
| (IV) | 36165 | 4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-amine; 4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-ylamine | C17H24N2O4 | 详情 | 详情 | |
| (V) | 11019 | (Methylimino)(oxo)methane; methyl isocyanate | C2H3NO | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(II)N-(Benzyloxycarbonyl)isonipecotic acid (I) was activated as the acid chloride (II) employing oxalyl chloride in the presence of a catalytic amount of DMF. Addition of diazomethane to acid chloride (II) produced the intermediate diazo ketone (III) which, upon treatment with an ethereal solution of HCl, led to the chloromethyl ketone (IV).
| 【1】 De Laszlo, S.E.; Mantlo, N.B.; Ponticello, G.S.; Selnick, H.G.; Liverton, N.J. (Merck & Co., Inc.); 2-Substd. aryl pyrroles, compsns. containing such cpds. and methods of use. EP 0863757; JP 1999510510; US 5792778; WO 9705877 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 56082 | Z-Isonipecotic acid | 10314-98-4 | C14H17NO4 | 详情 | 详情 |
| (II) | 36165 | 4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-amine; 4,7-dimethoxy-6-[2-(1-piperidinyl)ethoxy]-1-benzofuran-5-ylamine | C17H24N2O4 | 详情 | 详情 | |
| (III) | 56083 | benzyl 4-(2-diazoacetyl)-1-piperidinecarboxylate | C15H17N3O3 | 详情 | 详情 | |
| (IV) | 56084 | benzyl 4-(2-chloroacetyl)-1-piperidinecarboxylate | C15H18ClNO3 | 详情 | 详情 |