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【结 构 式】 
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【分子编号】33604 【品名】N-(3-chloro-3-phenylpropyl)-N,N-dimethylamine; 3-chloro-N,N-dimethyl-3-phenyl-1-propanamine 【CA登记号】 |
【 分 子 式 】C11H16ClN 【 分 子 量 】197.70748 【元素组成】C 66.83% H 8.16% Cl 17.93% N 7.08% |
合成路线1
该中间体在本合成路线中的序号：(III)The reduction of beta-dimethylaminopropiophenone (I) with diborane in THF gives N,N-dimethyl-3-phenyl-3-hydroxypropylamine (II), which is converted into N,N-dimethyl-3-phenyl-3-chloropropylamine (III) wtih refluxing SOCl2. The condensation of 4-trifluoromethylphenol (A) with (III) by means of NaOH in refluxing methanol affords N,N-dimethyl-3-phenyl-3-(p-trifluoromethylphenoxy) propylamine (IV), which is treated with BrCN in benzene to yield N-methyl-N-cyano-3-phenyl-3-(p-trifluoromethylphenoxy)propylamine (V). Finally, (V) is hydrolyzed with KOH in ethylene glycol at 130 C.
| 【1】 Molloy, B.B.; Schmiegel, K.K. (Eli Lilly and Company); Arloxyphenylpropylamines. DE 2500110; ES 433720; FR 2257288; GB 1493961; JP 50101333; US 4314081 . |
| 【2】 Paton, D.M.; Castaner, J.; Fluoxetine. Drugs Fut 1977, 2, 1, 27. |
| 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) | 33607 | 4-(trifluoromethyl)phenol | 402-45-9 | C7H5F3O | 详情 | 详情 |
| (I) | 33602 | 3-(Dimethylamino)propiophenone; beta-Dimethylaminopropiophenone; 3-(dimethylamino)-1-phenyl-1-propanone | 879-72-1 | C11H15NO | 详情 | 详情 |
| (II) | 33603 | 3-(dimethylamino)-1-phenyl-1-propanol | C11H17NO | 详情 | 详情 | |
| (III) | 33604 | N-(3-chloro-3-phenylpropyl)-N,N-dimethylamine; 3-chloro-N,N-dimethyl-3-phenyl-1-propanamine | C11H16ClN | 详情 | 详情 | |
| (IV) | 33605 | N,N-dimethyl-N-[3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]amine; N,N-dimethyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]-1-propanamine | C18H20F3NO | 详情 | 详情 | |
| (V) | 33606 | methyl[3-phenyl-3-[4-(trifluoromethyl)phenoxy]propyl]cyanamide | C18H17F3N2O | 详情 | 详情 |