N,N-diethyl-4-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]anilino]benzamide -Drug Synthesis Database

【结构式】

【分子编号】51371

【品名】N,N-diethyl-4-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]anilino]benzamide

【CA登记号】

【分子式】C₂₅H₃₃N₃O

【分子量】391.55664

【元素组成】C 76.69% H 8.49% N 10.73% O 4.09%

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：(VII)

The reductive alkylation of tropinone (I) with aniline (II) using either NaBH4 or NaBH(OAc)3 as the reducing agent furnished the endo-isomer (III). Arylation of amine (III) with t-butyl 4-bromobenzoate (IV) produced the (diarylamino)tropane (V). Acid cleavage of the tert-butyl ester of (V) gave acid (VI), which was further coupled to diethylamine, yielding amide (VII). Demethylation of tropane (VII) with 1-chloroethyl chloroformate, followed by methanolysis of the resulting carbamate (VIII), provided the secondary amine (IX). This was finally subjected to reductive alkylation with 3,4-methylenedioxybenzaldehyde (X) to give the title compound.

参考文献中间体

合成目标

【1】 Gauthier, A.D.; Neilson, L.A.; Carson, J.R.; Codd, E.E.; Zhang, S.-P.; Boyd, R.E.; Synthesis and binding affinities of 4-diarylaminotropanes, a new class of delta opioid agonists. Bioorg Med Chem Lett 2000, 10, 10, 1109.

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)	16443	(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-one		C₈H₁₃NO	详情	详情
(II)	12294	Aniline; Phenylamine	62-53-3	C₆H₇N	详情	详情
(III)	51368	(1R,5S)-8-methyl-N-phenyl-8-azabicyclo[3.2.1]octan-3-amine; N-[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]-N-phenylamine		C₁₄H₂₀N₂	详情	详情
(IV)	14286	tert-butyl 4-bromobenzoate		C₁₁H₁₃BrO₂	详情	详情
(V)	51369	tert-butyl 4-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]anilino]benzoate		C₂₅H₃₂N₂O₂	详情	详情
(VI)	51370	4-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]anilino]benzoic acid		C₂₁H₂₄N₂O₂	详情	详情
(VII)	51371	N,N-diethyl-4-[[(1R,5S)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl]anilino]benzamide		C₂₅H₃₃N₃O	详情	详情
(VIII)	51372	1-chloroethyl (1R,5S)-3-[4-[(diethylamino)carbonyl](phenyl)anilino]-8-azabicyclo[3.2.1]octane-8-carboxylate		C₂₇H₃₄ClN₃O₃	详情	详情
(IX)	51373	4-[(1R,5S)-8-azabicyclo[3.2.1]oct-3-ylanilino]-N,N-diethylbenzamide		C₂₄H₃₁N₃O	详情	详情
(X)	10127	1,3-Benzodioxole-5-carbaldehyde; Heliotropine	120-57-0	C₈H₆O₃	详情	详情

Extended Information