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【结 构 式】 
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【分子编号】61361 【品名】 【CA登记号】 |
【 分 子 式 】C15H26N2O3 【 分 子 量 】282.38312 【元素组成】C 63.8% H 9.28% N 9.92% O 17% |
合成路线1
该中间体在本合成路线中的序号：(XIV)Acylation of 4-amino-1-benzylpiperidine (X) with 5-chloropentanoyl chloride (XI) gives the chloro amide (XII), which is further cyclized to the 2-piperidone (XIII) in the presence of NaH. Replacement of the N-benzyl (XIII) for a N-Boc (XIV) protecting group is then accomplished by catalytic hydrogenolysis in the presence of Boc2O (1,2). Alkylation of piperidone (XIV) with allyl bromide (XV) yields the racemic 3-allyl-2-piperidone (XVI), which is subjected to oxidative cleavage with RuO2/NaIO4, producing carboxylic acid (XVII). After coupling of acid (XVII) with methylamine, the resultant N-methyl amide (XVIII) is deprotected by treatment with trifluoroacetic acid to give piperidine (XIX)
| 【1】 Ting, P.C.; Lee, J.F.; Shih, N.-Y.; et al.; Identification of a novel 1'-[5-((3,5-dichlorobenzoyl)methylamino)-3-(3,4-dichlorophenyl)-4-(methoxyimino)pentyl]- 2-oxo-(1,4'-bipiperidine) as a dual NK(1)/NK(2) antagonist. Bioog. Med. Chem. Lett. 2002, 12, 16, 2125. |
| 【2】 Carruthers, N.I.; Alaimo, C.A.; Shih, N.-Y.; Lavey, B.J.; Ting, P.C.; Reichard, G.A. (Schering Corp.); Substd. oximes as neurokinin antagonists. EP 1032561; WO 9926924 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (X) | 34809 | N-benzoyl-N'-(1-benzyl-4-piperidinyl)urea | C20H23N3O2 | 详情 | 详情 | |
| (XI) | 44277 | 5-chloropentanoyl chloride | 1575-61-7 | C5H8Cl2O | 详情 | 详情 |
| (XII) | 44278 | N-(1-benzyl-4-piperidinyl)-5-chloropentanamide | C17H25ClN2O | 详情 | 详情 | |
| (XIII) | 44279 | C17H24N2O | 详情 | 详情 | ||
| (XIV) | 61361 | C15H26N2O3 | 详情 | 详情 | ||
| (XVI) | 61362 | C18H30N2O3 | 详情 | 详情 | ||
| (XVII) | 61352 | C17H28N2O5 | 详情 | 详情 | ||
| (XVIII) | 61353 | C18H31N3O4 | 详情 | 详情 | ||
| (XIX) | 61354 | C13H23N3O2 | 详情 | 详情 |