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【结 构 式】 
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【分子编号】24052 【品名】N-butyl-2-(3,4-dimethoxyphenyl)-N-propylacetamide 【CA登记号】 |
【 分 子 式 】C17H27NO3 【 分 子 量 】293.40632 【元素组成】C 69.59% H 9.28% N 4.77% O 16.36% |
合成路线1
该中间体在本合成路线中的序号：(IV)3,4-Dimethoxyphenylacetyl chloride (II), obtained by the reaction of SOCl2 with 3,4-dimethoxyphenylacetic acid (I), is reacted with an excess of N-n-propyl-N-n-butylamine (III) in dry DMF to yield the corresponding amide. Following its extraction with ether from an aqueous solution, the amide (IV) is reduced to the corresponding amine (V) by refluxing in dry THF with 1.0 M diborane. The methyl protective groups are removed by refluxing the amine salt for less than 1 h with 56% HI in acetic anhydride. The deprotected amine obtained by neutralizing the hydroiodic salt with aqueous NaHCO3 is then converted to its hydrochloride salt. The final compound is recrystallized from ethanol ether.
| 【1】 Ginos, J.Z.; et al.; Cholinergic effects of molecular segments of apomorphine and dopaminergic effects of N,N-dialkylated dopamines. J Med Chem 1975, 18, 12, 1194. |
| 【2】 Ginos, J.Z.; et al.; New dopaminergic and potential anti-parkinson compounds, N,N-disubstituted beta-(3,4-dihydroxyphenyl)ethylamines. J Med Chem 1978, 21, 2, 160. |
| 【3】 Ginos, J.Z.; Propylbutyldopamine hydrochloride. Drugs Fut 1986, 11, 3, 191. |
| 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) | 24049 | 2-(3,4-dimethoxyphenyl)acetic acid | 93-40-3 | C10H12O4 | 详情 | 详情 |
| (II) | 20594 | 2-(3,4-dimethoxyphenyl)acetyl chloride | C10H11ClO3 | 详情 | 详情 | |
| (III) | 24051 | N-butyl-N-propylamine | 20193-21-9 | C7H17N | 详情 | 详情 |
| (IV) | 24052 | N-butyl-2-(3,4-dimethoxyphenyl)-N-propylacetamide | C17H27NO3 | 详情 | 详情 | |
| (V) | 24053 | N-(3,4-dimethoxyphenethyl)-N-propyl-1-butanamine | C17H29NO2 | 详情 | 详情 |