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【结 构 式】

【分子编号】48383

【品名】1-benzyl-4-(2-pyridinyl)-4-piperidinecarboxamide

【CA登记号】

【 分 子 式 】C18H21N3O

【 分 子 量 】295.38436

【元素组成】C 73.19% H 7.17% N 14.23% O 5.42%

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:(IV)

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
Extended Information