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【结 构 式】

【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%

与该中间体有关的原料药合成路线共 1 条

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
Extended Information