- 【药物名称】WB-4101
- 【化学名】2-[2-(2,6-Dimethoxyphenoxy)ethylaminomethyl]-1,4-benzodioxane
- 【CAS登记号】
- 【结构式】
- 【分子式】C19-H23-N-O5
- 【分子量】345.3927
- 【原研厂家】
- 【作用类别】alpha1-Adrenoceptor Antagonists
- 【研发状态】Not Determined
- 【合成情况】
- 〖来源〗J Med Chem
- 〖合成路线〗
- 〖标题〗Synthesis and pharmacological properties of a series of 2-(substituted-aminoethyl)-1,4-benzodioxanes
- 〖合成方法〗By condensation of 2-aminomethyl-1,4-benzodioxane (I) with 2,6-dimethoxyphenoxyethyl chloride (II) performed by heating at 160 C or by means of K2CO3 in refluxing CHCl3 - water. The starting products (I) and (II) are prepared as follows: 1) The reaction of 2-chloromethyl-1,4-benzodioxane (III) with potassium phthalimide (IV) in refluxing DMF gives 2-phthalimidomethyl-1,4-benzodioxane (V), which is then treated with hydrazine hydrate (A) in refluxing 2-ethoxyethanol to give (I). 2) The condensation of 2,6-dimethoxyphenol (VI) with ethylene carbonate (VII) by means of K2CO3 in refluxing toluene gives 2,6-dimethoxyphenoxyethanol (VIII), which is then refluxed with SOCl2 to afford (II).
- 〖作者〗Green, P.N.; et al.
- 〖参考〗Green, P.N.; et al.; Synthesis and pharmacological properties of a series of 2-(substituted-aminoethyl)-1,4-benzodioxanes. J Med Chem 1969, 12, 2, 326-329
- 〖出处〗J Med Chem1969,12,(2):326-329
- 〖备注〗
- 〖来源〗Drugs Fut
- 〖合成路线〗
- 〖标题〗WB-4101
- 〖合成方法〗By condensation of 2-aminomethyl-1,4-benzodioxane (I) with 2,6-dimethoxyphenoxyethyl chloride (II) performed by heating at 160 C or by means of K2CO3 in refluxing CHCl3 - water. The starting products (I) and (II) are prepared as follows: 1) The reaction of 2-chloromethyl-1,4-benzodioxane (III) with potassium phthalimide (IV) in refluxing DMF gives 2-phthalimidomethyl-1,4-benzodioxane (V), which is then treated with hydrazine hydrate (A) in refluxing 2-ethoxyethanol to give (I). 2) The condensation of 2,6-dimethoxyphenol (VI) with ethylene carbonate (VII) by means of K2CO3 in refluxing toluene gives 2,6-dimethoxyphenoxyethanol (VIII), which is then refluxed with SOCl2 to afford (II).
- 〖作者〗Castaer, J.; Serradell, M.N.; Hillier, K.; Blancafort, P.
- 〖参考〗Castaer, J.; Serradell, M.N.; Hillier, K.; Blancafort, P.; WB-4101. Drugs Fut 1979, 4, 5, 369
- 〖出处〗Drugs Fut1979,4,(5):369
- 〖备注〗Synthesis By condensation of 2-aminomethyl-1,4-benzodioxane (I) with 2,6-dimethoxyphenoxyethyl chloride (II) performed by heating at 160?(1) or by means of K2CO3 in refluxing CHCl3 - water (2). The starting products (I) and (II) are prepared as follows: 1) The reaction of 2-chloromethyl-1,4-benzodioxane (III) with potassium phthalimide (IV) in refluxirig DMF gives 2-phthalimidomethyl-1,4-benzodioxane (V), which is then treated with hydrazine hydrate (A) in refluxing 2-ethoxyethanol to give (I) (1). 2) The condensation of 2,6-dimethoxyphenol (VI) with ethylene carbonate (VII) by means of K2CO3 in refluxing toluene gives 2,6-dimethoxyphenoxyethanol (VIII), which is then refluxed with SOCl2 to afford (II) (1). Description Yellow viscous oil, b.p.(1 mm) = 234-8? HCl salt, m.p. 155-7?(1). Manufacturer Ward Blenkinsop Pharmaceuticals, London (England) References 1. Green, P.N. et al.; Synthesis and pharmacological properties of a series of 2-(substituted-aminoethyl)-1,4-benzodioxanes; J Med Chem 1969, 12(2), 326-329 2. Ward Blenkinsop & Co., Ltd.; US 3472874
- 〖来源〗US 3472874
- 〖合成路线〗
- 〖标题〗
- 〖合成方法〗By condensation of 2-aminomethyl-1,4-benzodioxane (I) with 2,6-dimethoxyphenoxyethyl chloride (II) performed by heating at 160 C or by means of K2CO3 in refluxing CHCl3 - water. The starting products (I) and (II) are prepared as follows: 1) The reaction of 2-chloromethyl-1,4-benzodioxane (III) with potassium phthalimide (IV) in refluxing DMF gives 2-phthalimidomethyl-1,4-benzodioxane (V), which is then treated with hydrazine hydrate (A) in refluxing 2-ethoxyethanol to give (I). 2) The condensation of 2,6-dimethoxyphenol (VI) with ethylene carbonate (VII) by means of K2CO3 in refluxing toluene gives 2,6-dimethoxyphenoxyethanol (VIII), which is then refluxed with SOCl2 to afford (II).
- 〖作者〗
- 〖参考〗; . US 3472874
- 〖出处〗US 3472874,,():
- 〖备注〗
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