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【结 构 式】 
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【分子编号】36544 【品名】4-(aminomethyl)-1-benzyl-4-piperidinol 【CA登记号】 |
【 分 子 式 】C13H20N2O 【 分 子 量 】220.31468 【元素组成】C 70.87% H 9.15% N 12.72% O 7.26% |
合成路线1
该中间体在本合成路线中的序号：(XV)4-(Aminomethyl)-1-benzyl-4-hydroxypiperidine (XV) was protected as the tert-butyl carbamate (XVI) and the benzyl group was subsequently cleaved by transfer hydrogenolysis employing ammonium formate and Pd/C yielding (XVII). Condensation of piperidine (XVII) with mesylate (VIII) in the presence of K2CO3 in boiling isopropanol furnished adduct (XVIII). After deprotection of the Boc group of (XVIII) with trifluoroacetic acid, reductive alkylation of the resulting amine (XIX) with benzaldehyde in the presence of NaBH3CN provided the N-benzyl amine (XX). Finally, a further reductive alkylation of (XX) with formaldehyde and NaBH3CN yielded the title compound.
| 【1】 Stanton, J.A.; Showell, G.A.; Neduvelil, J.G.; Bourrain, S.; Beer, M.S.; MacLeod, A.M.; 4-Hydroxy-1-[3-(5-(1,2,4-triazol-4-yl)-1H-indol-3-yl)propyl]piperidines: Selective h5-HT1D agonists for the treatment of migraine. Bioorg Med Chem Lett 1999, 9, 23, 3369. |
| 【2】 Baker, R.; Bourrain, S.; Castro Pineiro, J.L.; Chambers, M.S.; Guiblin, A.R.; Hobbs, S.C.; Jelley, R.A.; Madin, A.; Matassa, V.G.; Reeve, A.J.; Russell, M.G.N.; Showell, G.A.; Sternfeld, F.; Street, L.J.; Van Niel, M.B. (Merck Sharp & Dohme Ltd.); Azetidine, pyrrolidine and piperidine derivs.. EP 0804434; JP 1998503768; US 5854268; WO 9604274 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| 10498 | Benzaldehyde;Benzoic aldehyde;Phenylmethanal | 100-52-7 | C7H6O | 详情 | 详情 | |
| (VIII) | 36539 | 3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl methanesulfonate | C14H16N4O3S | 详情 | 详情 | |
| (XV) | 36544 | 4-(aminomethyl)-1-benzyl-4-piperidinol | C13H20N2O | 详情 | 详情 | |
| (XVI) | 36545 | tert-butyl (1-benzyl-4-hydroxy-4-piperidinyl)methylcarbamate | C18H28N2O3 | 详情 | 详情 | |
| (XVII) | 36546 | tert-butyl (4-hydroxy-4-piperidinyl)methylcarbamate | C11H22N2O3 | 详情 | 详情 | |
| (XVIII) | 36547 | tert-butyl (4-hydroxy-1-[3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl]-4-piperidinyl)methylcarbamate | C24H34N6O3 | 详情 | 详情 | |
| (XIX) | 36548 | 4-(aminomethyl)-1-[3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl]-4-piperidinol | C19H26N6O | 详情 | 详情 | |
| (XX) | 36549 | 4-[(benzylamino)methyl]-1-[3-[5-(4H-1,2,4-triazol-4-yl)-1H-indol-3-yl]propyl]-4-piperidinol | C26H32N6O | 详情 | 详情 |