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【结 构 式】 
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【分子编号】48382 【品名】1-benzyl-4-(2-pyridinyl)-4-piperidinecarbonitrile 【CA登记号】 |
【 分 子 式 】C18H19N3 【 分 子 量 】277.36908 【元素组成】C 77.95% H 6.9% N 15.15% |
合成路线1
该中间体在本合成路线中的序号：(III)Condensation of 2-pyridylacetonitrile (I) with N,N-bis-(2-chloroethyl)benzylamine (II) under phase-transfer conditions produced the pyridylpiperidine (III). The cyano group of (III) was hydrolyzed to carboxamide (IV) with concentrated sulfuric acid and then decarboxylated to (V) by treatment with methanolic HCl. Subsequent hydrogenolysis of the N-benzyl group of (V) afforded piperidine (VI). N-Boc-3-bromopropylamine (VIII) was prepared by treatment of 3-bromopropylamine (VII) with di-tert-butyl dicarbonate. Alkylation of piperidine (VI) with bromide (VIII) gave adduct (IX). The N-Boc protecting group of (IX) was then removed by treatment with trifluoroacetic acid to yield intermediate aine (X).
| 【1】 Wong, W.C.; Lagu, B.; Nagarathnam, D.; Marzabadi, M.R.; Gluchowski, C. (Synaptic Pharmaceutical Corp.); Dihydropyrimidines and uses thereof. EP 1021185; JP 2000506904; WO 9742956 . |
| 【2】 Lagu, B.; Nagarathnam, D.; Marzabadi, M.R.; Wong, W.C.; Gluchowski, C. (Synaptic Pharmaceutical Corp.); Dihydropyrimidines and uses thereof. WO 9851311 . |
| 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) | 36179 | 2-(2-pyridinyl)acetonitrile | C7H6N2 | 详情 | 详情 | |
| (II) | 23122 | N-benzyl-2-chloro-N-(2-chloroethyl)-1-ethanamine; N-Benzylbis(2-chloroethyl)amine | 10429-82-0 | C11H15Cl2N | 详情 | 详情 |
| (III) | 48382 | 1-benzyl-4-(2-pyridinyl)-4-piperidinecarbonitrile | C18H19N3 | 详情 | 详情 | |
| (IV) | 48383 | 1-benzyl-4-(2-pyridinyl)-4-piperidinecarboxamide | C18H21N3O | 详情 | 详情 | |
| (V) | 48384 | 1-benzyl-4-(2-pyridinyl)piperidine | C17H20N2 | 详情 | 详情 | |
| (VI) | 48385 | 2-(4-piperidinyl)pyridine | C10H14N2 | 详情 | 详情 | |
| (VII) | 25449 | 3-bromo-1-propanamine; 3-bromopropylamine | 18370-81-5 | C3H8BrN | 详情 | 详情 |
| (VIII) | 37752 | tert-butyl 3-bromopropylcarbamate | C8H16BrNO2 | 详情 | 详情 | |
| (IX) | 48386 | tert-butyl 3-[4-(2-pyridinyl)-1-piperidinyl]propylcarbamate | C18H29N3O2 | 详情 | 详情 | |
| (X) | 48387 | 3-[4-(2-pyridinyl)-1-piperidinyl]propylamine; 3-[4-(2-pyridinyl)-1-piperidinyl]-1-propanamine | C13H21N3 | 详情 | 详情 |