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【结 构 式】 
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【分子编号】57813 【品名】3-(4-chlorophenyl)-3-(2-pyridinyl)propylamine; 3-(4-chlorophenyl)-3-(2-pyridinyl)-1-propanamine 【CA登记号】 |
【 分 子 式 】C14H15ClN2 【 分 子 量 】246.73928 【元素组成】C 68.15% H 6.13% Cl 14.37% N 11.35% |
合成路线1
该中间体在本合成路线中的序号：(V)The unsaturated nitrile (III) is prepared by Wittig reaction of 2-(4-chlorobenzoyl)pyridine (I) with phosphorane (II). Subsequent reduction of (III) with NaBH4 in boiling isopropanol provides the saturated nitrile (IV). The cyano group of (IV) is then reduced to amine (V) employing LiAlH4 in refluxing Et2O.
| 【1】 Tom, W.; Aslanian, R.; West, R.; Shih, N.-Y.; Piwinski, J.J.; She, S.; Williams, S.M.; Design and synthesis of novel dual histamine H1/H3 receptor antagonists based on the H1 receptor antagonist chlorpheniramine. 223rd ACS Natl Meet (April 7 2002, Orlando) 2002, Abst MEDI 63. |
| 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) | 57809 | 4-(4-Chlorobenzoyl)pyridine; 4-Chlorophenyl 4-pyridyl ketone | 14548-48-2 | C12H8ClNO | 详情 | 详情 |
| (II) | 57810 | 2-(triphenylphosphoranylidene)acetonitrile | C20H16NP | 详情 | 详情 | |
| (III) | 57811 | (Z)-3-(4-chlorophenyl)-3-(2-pyridinyl)-2-propenenitrile | C14H9ClN2 | 详情 | 详情 | |
| (IV) | 57812 | 3-(4-chlorophenyl)-3-(2-pyridinyl)propanenitrile | C14H11ClN2 | 详情 | 详情 | |
| (V) | 57813 | 3-(4-chlorophenyl)-3-(2-pyridinyl)propylamine; 3-(4-chlorophenyl)-3-(2-pyridinyl)-1-propanamine | C14H15ClN2 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(V)Metalation of 1-trityl-4-iodoimidazole (VI) with ethylmagnesium bromide, followed by addition to 4-cyanobenzaldehyde (VII) gives rise to the carbinol (VIII), which is further reduced to the diaryl methane (IX) employing triibutyltin hydride in the presence of AIBN. Trimethylaluminium-catalyzed coupling between nitrile (IX) and amine (V) provides amidine (X). The N-trityl group of (X) is finally removed under acidic conditions to furnish the title compound.
| 【1】 Tom, W.; Aslanian, R.; West, R.; Shih, N.-Y.; Piwinski, J.J.; She, S.; Williams, S.M.; Design and synthesis of novel dual histamine H1/H3 receptor antagonists based on the H1 receptor antagonist chlorpheniramine. 223rd ACS Natl Meet (April 7 2002, Orlando) 2002, Abst MEDI 63. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (V) | 57813 | 3-(4-chlorophenyl)-3-(2-pyridinyl)propylamine; 3-(4-chlorophenyl)-3-(2-pyridinyl)-1-propanamine | C14H15ClN2 | 详情 | 详情 | |
| (VI) | 30216 | 4-iodo-1-trityl-1H-imidazole | C22H17IN2 | 详情 | 详情 | |
| (VII) | 17552 | 4-formylbenzonitrile; 4-Cyanobenzaldehyde | 105-07-7 | C8H5NO | 详情 | 详情 |
| (VIII) | 57814 | 4-[hydroxy(1-trityl-1H-imidazol-4-yl)methyl]benzonitrile | C30H23N3O | 详情 | 详情 | |
| (IX) | 57815 | 4-[(1-trityl-1H-imidazol-4-yl)methyl]benzonitrile | C30H23N3 | 详情 | 详情 | |
| (X) | 57816 | N-[3-(4-chlorophenyl)-3-(2-pyridinyl)propyl]-4-[(1-trityl-1H-imidazol-4-yl)methyl]benzenecarboximidamide | C44H38ClN5 | 详情 | 详情 |