Diphenylamine; N-phenylaniline; N,N-diphenylamine -Drug Synthesis Database

【结构式】

【分子编号】42251

【品名】Diphenylamine; N-phenylaniline; N,N-diphenylamine

【CA登记号】122-39-4

【分子式】C₁₂H₁₁N

【分子量】169.22608

【元素组成】C 85.17% H 6.55% N 8.28%

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：(I)

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.

参考文献中间体

合成目标

【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