• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】23304

【品名】1-benzyl-4-piperidinol; 1-benzyl-4-hydroxypiperidine; N-Benzyl-4-hydroxypiperidine; 1-(benzyl)-4-piperidinol

【CA登记号】4727-72-4

【 分 子 式 】C12H17NO

【 分 子 量 】191.27312

【元素组成】C 75.35% H 8.96% N 7.32% O 8.36%

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)

Treatment of 2,2-diphenylacetic acid (I) with diphenyl phosphoryl azide (DPPA) yielded acyl azide (II). Then, Curtius rearrangement of (II) in boiling toluene produced the intermediate isocyanate (III), which was coupled with 1-benzyl-4-piperidinol (IV) to afford the corresponding carbamate (V). Subsequent N-debenzylation of (V) was achieved by reaction with 1-chloroethyl chloroformate in refluxing 1,2-dichloroethane, followed by methanolysis to give (VI). Reductive alkylation of (VI) with aldehyde (VII) in the presence of sodium triacetoxyborohydride furnished the substituted benzyl piperidine (VIII). The N-Boc protecting group of (VIII) was finally removed with ethanolic HCl to provide the title compound.

1 Naito, R.; Takeuchi, M.; Morihira, K.; Hayakawa, M.; Ikeda, K.; Shibanuma, T.; Isomura, Y.; Selective muscarinic antagonists. I. Synthesis and. Chem Pharm Bull 1998, 46, 8, 1274.
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) 19827 2,2-diphenylacetic acid 117-34-0 C14H12O2 详情 详情
(II) 23302 2,2-diphenylacetyl azide C14H11N3O 详情 详情
(III) 23303 1-[isocyanato(phenyl)methyl]benzene; benzhydryl isocyanate C14H11NO 详情 详情
(IV) 23304 1-benzyl-4-piperidinol; 1-benzyl-4-hydroxypiperidine; N-Benzyl-4-hydroxypiperidine; 1-(benzyl)-4-piperidinol 4727-72-4 C12H17NO 详情 详情
(V) 23305 1-benzyl-4-piperidinyl benzhydrylcarbamate C26H28N2O2 详情 详情
(VI) 23306 4-piperidinyl benzhydrylcarbamate C19H22N2O2 详情 详情
(VII) 23307 tert-butyl 4-formylphenyl(methyl)carbamate C13H17NO3 详情 详情
(VIII) 23308 1-[4-[(tert-butoxycarbonyl)(methyl)amino]benzyl]-4-piperidinyl benzhydrylcarbamate C32H39N3O4 详情 详情
Extended Information