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【结 构 式】

【分子编号】42253

【品名】N-phenyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]aniline; N,N-diphenyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]amine

【CA登记号】

【 分 子 式 】C20H25NO2

【 分 子 量 】311.42404

【元素组成】C 77.14% H 8.09% N 4.5% O 10.27%

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:(III)

Alkylation of diphenylamine (I) with THP-protected 3-bromopropanol (II) using NaH in 15-crown-5 yields tertiary amine (III), which is then deprotected with HOAc/H2O to provide (IV). Alcohol (IV) is treated with PPh3 and CBr4 to afford alkyl bromide (V), which is then converted into amine (VII) by reaction with 2,6-dimethylpiperazine (VI) in DMF/H2O in the presence of K2CO3. Finally, (VII) is acylated with 3-phenylpropionyl chloride (VIII) and reduced with LAH.

1 Vilner, B.J.; Husbands, S.M.; Bowen, W.D.; Newman, A.H.; Kopajtic, T.; Izenwasser, S.; Katz, J.L.; Structure-activity relationships at the monoamine transporters and sigma receptors for a novel series of 9-[3-(cis-3,5-dimethyl-1-piperazinyl)-propyl]carbazole (rimcazole) analogues. J Med Chem 1999, 42, 21, 4446.
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) 42251 Diphenylamine; N-phenylaniline; N,N-diphenylamine 122-39-4 C12H11N 详情 详情
(II) 42252 3-bromopropyl tetrahydro-2H-pyran-2-yl ether; 2-(3-bromopropoxy)tetrahydro-2H-pyran C8H15BrO2 详情 详情
(III) 42253 N-phenyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]aniline; N,N-diphenyl-N-[3-(tetrahydro-2H-pyran-2-yloxy)propyl]amine C20H25NO2 详情 详情
(IV) 42254 3-(diphenylamino)-1-propanol C15H17NO 详情 详情
(V) 42255 N-(3-bromopropyl)-N-phenylaniline; N-(3-bromopropyl)-N,N-diphenylamine C15H16BrN 详情 详情
(VI) 20848 (2R,6S)-2,6-dimethylpiperazine C6H14N2 详情 详情
(VII) 42256 N-[3-[(3R,5S)-3,5-dimethylpiperazinyl]propyl]-N,N-diphenylamine; N-[3-[(3R,5S)-3,5-dimethylpiperazinyl]propyl]-N-phenylaniline C21H29N3 详情 详情
(VIII) 16240 3-phenylpropanoyl chloride; Hydrocinnamoylchloride 645-45-4 C9H9ClO 详情 详情
Extended Information