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【结 构 式】

【分子编号】21579

【品名】(7-chloro-5-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl benzoate

【CA登记号】

【 分 子 式 】C16H12ClNO6

【 分 子 量 】349.72712

【元素组成】C 54.95% H 3.46% Cl 10.14% N 4.01% O 27.45%

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:(VI)

Flesinoxan hydrochloride is obtained in a multiple-step synthesis, including the resolution of one of the racemic intermediates (VIII), starting with the monobenzyl ether of catechol (I). Treatment of (I) with sulfuryl chloride in methylene chloride gives (II). This chloro compound is nitrated with nitric acid resulting in the mononitro derivative (III). In a one-pot procedure compound (III) is converted to the racemic benzodioxan structure (V) by condensation with epichlorohydrin, followed by treatment of the intermediate (IV) with hydrochloric acid and with potassium hydroxide, respectively. After conversion of the hydroxymethyl derivative to the benzoic ester (VI), compound (VII) can be obtained by catalytic hydrogenation of (VI). Treatment of (VII) with bischloroethylamine results in the racemic piperazine analogue (VIII). In this phase the resolution of the piperazine is carried out with (+)-camphorsulfonic acid. After several recrystallizations, the optically pure (+)-enantiomer is obtained. Reaction of this (+)-N-[2-(hydroxymethyl)-1,4-benzodioxan-5-yl]piperazine (VIII) with N-(4-fluorobenzoyl)aziridine, saponification of the benzoate ester and treatment with hydrochloric acid gives flesinoxan monohydrochloride.

1 Hartog, J.; Wouters, W.; FLESINOXAN HYDROCHLORIDE < Rec INN >. Drugs Fut 1988, 13, 1, 31.
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) 15209 Phenol, 2-(phenylmethoxy)-; 2-(benzyloxy)phenol 6272-38-4 C13H12O2 详情 详情
(II) 21575 2-(benzyloxy)-4-chlorophenol C13H11ClO2 详情 详情
(III) 21576 2-(benzyloxy)-4-chloro-6-nitrophenol C13H10ClNO4 详情 详情
(IV) 21577 2-[[2-(benzyloxy)-4-chloro-6-nitrophenoxy]methyl]oxirane; benzyl 5-chloro-3-nitro-2-(2-oxiranylmethoxy)phenyl ether C16H14ClNO5 详情 详情
(V) 21578 (7-chloro-5-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methanol C9H8ClNO5 详情 详情
(VI) 21579 (7-chloro-5-nitro-2,3-dihydro-1,4-benzodioxin-2-yl)methyl benzoate C16H12ClNO6 详情 详情
(VII) 21580 (5-amino-2,3-dihydro-1,4-benzodioxin-2-yl)methyl benzoate C16H15NO4 详情 详情
(VIII) 21581 [5-(1-piperazinyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl benzoate C20H22N2O4 详情 详情
(IX) 10146 Epichlorohydrin; 2-(Chloromethyl)oxirane 106-89-8 C3H5ClO 详情 详情
(X) 21583 2-chloro-N-(2-chloroethyl)-1-ethanamine; Bis(2-chloroethyl)amine; 1,1'-iminobis(2-chloroethane); N,N-bis(2-chloroethyl)amine 821-48-7 C4H9Cl2N 详情 详情
Extended Information