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【结 构 式】

【分子编号】35994

【品名】3-(3-hydroxyphenyl)-1-propyl-2,6-piperidinedione

【CA登记号】

【 分 子 式 】C14H17NO3

【 分 子 量 】247.29392

【元素组成】C 68% H 6.93% N 5.66% O 19.41%

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:(XV)

The condensation of (3-methoxyphenyl)acetonitrile (VIII) with 3-bromopropyltetrahydropyranyl ether (IX) by means of lithium diisopropylamide in THF gives 2-(3-methoxyphenyl)-5-tetrahydropyranyloxypentanonitrile (X), which is oxidized with chromic anhydride-H2SO4 yielding 4-cyano-3-(3-methoxyphenyl)butyric acid (XI). The hydrolysis of (XI) with KOH in ethanol-water affords 2-(3-methoxyphenyl)glutaric acid (XII), which is anhydrized with refluxing acetic anhydride giving 2-(3-methoxyphenyl)glutaric anhydride (XIII). The reaction of (XIII) with propylamine (C) in refluxing benzene yields 2-(3-methoxyphenyl)-N-propylglutarimide (XIV), which is demethylated with BBr3 in methylene chloride to 2-(3-hydroxyphenyl)-N-propylglutarimide (XV). The benzylation of (XV) with benzyl bromide and K2CO3 in DMF affords 2-(3-benzyloxyphenyl)-N-propylglutarimide (XVI), which is reduced with LiAlH4 in THF giving 3-(3-benzyloxyphenyl)-N-propylpiperidine (XVII). Finally, this compound is debenzylated by hydrogenolysis with H2 over Pd/C in AcOH.

1 Brands, F.T.L.; Loozen, H.J.J.; An efficient synthesis of 3-arylpiperidines. J R Neth Chem Soc 1981, 100, 9, 333-336.
2 Serradell, M.N.; Nohria, V.; Castaner, J.; Blancafort, P.; 3-PPP. Drugs Fut 1983, 8, 1, 27.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
12912 1-(Bromomethyl)benzene; Alpha-bromotoluene 100-39-0 C7H7Br 详情 详情
(VIII) 24061 3-methoxyphenylacetonitrile; 2-(3-methoxyphenyl)acetonitrile 19924-43-7 C9H9NO 详情 详情
(IX) 29460 2-(4-bromobutoxy)tetrahydro-2H-pyran; 4-bromobutyl tetrahydro-2H-pyran-2-yl ether C9H17BrO2 详情 详情
(X) 35989 2-(3-methoxyphenyl)-6-(tetrahydro-2H-pyran-2-yloxy)hexanenitrile C18H25NO3 详情 详情
(XI) 35990 4-cyano-4-(3-methoxyphenyl)butyric acid C12H13NO3 详情 详情
(XII) 35991 2-(3-methoxyphenyl)pentanedioic acid C12H14O5 详情 详情
(XIII) 35992 3-(3-methoxyphenyl)dihydro-2H-pyran-2,6(3H)-dione C12H12O4 详情 详情
(XIV) 35993 3-(3-methoxyphenyl)-1-propyl-2,6-piperidinedione C15H19NO3 详情 详情
(XV) 35994 3-(3-hydroxyphenyl)-1-propyl-2,6-piperidinedione C14H17NO3 详情 详情
(XVI) 35995 3-[3-(benzyloxy)phenyl]-1-propyl-2,6-piperidinedione C21H23NO3 详情 详情
(XVII) 35996 benzyl 3-(1-propyl-3-piperidinyl)phenyl ether; 3-[3-(benzyloxy)phenyl]-1-propylpiperidine C21H27NO 详情 详情
(C) 23923 1-propanamine 107-10-8 C3H9N 详情 详情
Extended Information