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【结 构 式】

【分子编号】41969

【品名】2,6-di(tert-butyl)-4-methoxyphenyl 4-[[(3R,4S)-1,3-dimethylpiperidinyl]anilino]benzoate

【CA登记号】

【 分 子 式 】C35H46N2O3

【 分 子 量 】542.76192

【元素组成】C 77.45% H 8.54% N 5.16% O 8.84%

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:(V)

Condensation of 1,3-dimethyl-4-piperidone (I) with aniline in the presence of titanium tetraisopropoxide produced imine (II). This was reduced with NaBH4 to give the corresponding amine as a mixture of geometric isomers, from which the desired cis isomer (III) was isolated by column chromatography. Coupling of (III) with 4-fluorobenzoate ester (IV) in the presence of butyllithium yielded the diaryl amine (V). Removal of the 2,6-di-tert-butyl-4-methoxyphenyl ester of (V) was accomplished by transesterification with sodium methoxide, followed by saponification of the methyl ester. The resulting carboxylic acid (VI) was then converted into diethyl amide (VII) using diethylamine and BOP reagent. N-Demethylation of (VII) with phenyl chloroformate furnished the phenyl carbamate (VIII), that was further hydrolyzed and decarboxylated to give piperidine (IX). This was finally alkylated with allyl bromide in the presence of K2CO3.

1 Carroll, F.I.; Thomas, J.B.; Dersch, C.M.; Rothman, R.B.; Mascarella, S.W.; Burges, J.P.; Xu, H.; Herault, X.M.; Horel, R.B.; (±)-4-[(N-Allyl-cis-3-methyl-4-piperidinyl)phenylamino]-N,N-diethylbenzamide displays selective binding for the delta opioid receptor. Bioorg Med Chem Lett 1999, 9, 20, 3053.
2 Carroll, F.I.; Novel opiate cpds., methods of making and methods of use. WO 9945925 .
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) 16614 1,3-dimethyltetrahydro-4(1H)-pyridinone; 1,3-Dimethyl-4-piperidone 4629-80-5 C7H13NO 详情 详情
(II) 41966 N-(1,3-dimethyl-4-piperidinylidene)-N-phenylamine; N-(1,3-dimethyl-4-piperidinylidene)aniline C13H18N2 详情 详情
(III) 41968 N-[(3R,4S)-1,3-dimethylpiperidinyl]-N-phenylamine; (3R,4S)-1,3-dimethyl-N-phenyl-4-piperidinamine C13H20N2 详情 详情
(IV) 41458 2,6-di(tert-butyl)-4-methoxyphenyl 4-fluorobenzoate C22H27FO3 详情 详情
(V) 41969 2,6-di(tert-butyl)-4-methoxyphenyl 4-[[(3R,4S)-1,3-dimethylpiperidinyl]anilino]benzoate C35H46N2O3 详情 详情
(VI) 41970 4-[[(3R,4S)-1,3-dimethylpiperidinyl]anilino]benzoic acid C20H24N2O2 详情 详情
(VII) 41971 4-[[(3R,4S)-1,3-dimethylpiperidinyl]anilino]-N,N-diethylbenzamide C24H33N3O 详情 详情
(VIII) 41967 phenyl (3R,4S)-4-[4-[(diethylamino)carbonyl](phenyl)anilino]-3-methyl-1-piperidinecarboxylate C30H35N3O3 详情 详情
(IX) 41972 N,N-diethyl-4-[[(3R,4S)-3-methylpiperidinyl]anilino]benzamide C23H31N3O 详情 详情
Extended Information