2-(2-oxiranylmethoxy)benzonitrile -Drug Synthesis Database

【结构式】

【分子编号】37567

【品名】2-(2-oxiranylmethoxy)benzonitrile

【CA登记号】

【分子式】C₁₀H₉NO₂

【分子量】175.187

【元素组成】C 68.56% H 5.18% N 8% O 18.27%

与该中间体有关的原料药合成路线共 4 条

合成路线1 合成路线2 合成路线3 合成路线4

合成路线1

该中间体在本合成路线中的序号：(II)

By reaction of 3-(2-methyl-2-aminopropyl)indole (I) and 2-(2,3-epoxypropoxy)benzonitrile (II) by heating at 120-40 C followed by a treatment with HCl in ethanol. The starting products are obtained as follows: 1) The reaction of 3-(dimethylaminomethyl)indole (III) with 2-nitropropane (IV) by means of KOH gives 3-(2-methyl-2-nitropropyl)indole (V), which is then reduced with hydrazine and Raney-Ni in ethanol to yield (I). 2) The reaction of 2-hydroxybenzonitrile (VI) with epichlorohydrin (VII) by means of piperidine affords 2-(3-chloro-2-hydroxypropoxy)benzonitrile (VIII), which is epoxidized again to (II) by treatment with NaOH in hot THF-water.

参考文献中间体

合成目标

【1】 Kreighbaum, W.E.; et al.; Antihypertensive indole derivatives of phenoxypropanolamines with beta-adrenergic receptor antagonist and vasodilating activity. J Med Chem 1980, 23, 3, 285-289.
【2】 Weetman, D.F.; Castaner, J.; Bucindolol Hydrochloride. Drugs Fut 1981, 6, 7, 405.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	10158	Piperidine	110-89-4	C₅H₁₁N	详情	详情
(I)	37566	2-(1H-indol-3-yl)-1,1-dimethylethylamine; 1-(1H-indol-3-yl)-2-methyl-2-propanamine		C₁₂H₁₆N₂	详情	详情
(II)	37567	2-(2-oxiranylmethoxy)benzonitrile		C₁₀H₉NO₂	详情	详情
(III)	37568	N,N-Dimethyl-1H-indole-3-methanamine;Gramine;N-(1H-indol-3-ylmethyl)-N,N-dimethylamine; 3-(dimethylaminomethyl)-indole[;]1H-indol-3-yl-N,N-dimethylmethanamine	87-52-5	C₁₁H₁₄N₂	详情	详情
(IV)	21819	2-nitropropane	79-46-9	C₃H₇NO₂	详情	详情
(V)	37569	3-(2-methyl-2-nitropropyl)-1H-indole		C₁₂H₁₄N₂O₂	详情	详情
(VI)	21990	2-hydroxybenzonitrile	611-20-1	C₇H₅NO	详情	详情
(VII)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(VIII)	37570	2-(3-chloro-2-hydroxypropoxy)benzonitrile		C₁₀H₁₀ClNO₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

The condensation of 1-(2-cyanophenoxy)-2,3-epoxypropane (I) with ethylenediamine (II) gives 1-(2-cyanophenoxy)-3-(2-aminoethylamino)-2-propanol (III), which is finally treated with phenyl isocyanate (IV) in acetonitrile.

参考文献中间体

合成目标

【1】 Blancafort, P.; Serradell, M.N.; Castaner, J.; McGillion, F.B.; ICl-89,406. Drugs Fut 1981, 6, 9, 555.
【2】 Large, M.S.; Smith, L.H.; Beta-adrenergic blocking agents. 22. 1-Phenoxy-3-[[(substituted-amido)alkyl]amino]-2-propanols. J Med Chem 1982, 25, 11, 1286.

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)	37567	2-(2-oxiranylmethoxy)benzonitrile		C₁₀H₉NO₂	详情	详情
(II)	14754	ethylenediamine;1,2-Diaminoethane;ethane-1,2-diamine；1,2-Ethanediamine	107-15-3	C₂H₈N₂	详情	详情
(III)	61094	2-{3-[(2-aminoethyl)amino]-2-hydroxypropoxy}benzonitrile		C₁₂H₁₇N₃O₂	详情	详情
(IV)	11289	1-Isocyanatobenzene; phenyl isocyanate; Phenylisocyanate	103-71-9	C₇H₅NO	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

By condensation of 1-(2-cyanophenoxy)-2,3-epoxypropane (I) with 2-(3-phenylureido)ethylamine (II) in refluxing propanol.

参考文献中间体

合成目标

【1】 Smith, L.H. (Imperial Chem. Inds., Ltd.); BE 808666; CA 1031362; CH 611876; DE 2362568; FR 2210407; GB 1455116; HU 11305; JP 7494638; NL 7317096; US 3928412; US 4010189; US 4083992; US 4131685; US 4167581; ZA 7309205 .
【2】 Blancafort, P.; Serradell, M.N.; Castaner, J.; McGillion, F.B.; ICl-89,406. Drugs Fut 1981, 6, 9, 555.

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)	37567	2-(2-oxiranylmethoxy)benzonitrile		C₁₀H₉NO₂	详情	详情
(II)	61092	N-(2-aminoethyl)-N'-phenylurea		C₉H₁₃N₃O	详情	详情

合成路线4

该中间体在本合成路线中的序号：(II)

It can be prepared in several different ways: 3) By hydrolysis of 1-(2-cyanophenoxy)-2-hydroxy-3-(N-acetyl-N-tert-butylamino)propane (V) with KOH in refluxing ethanol. 4) By heating N,N'-di-tert-butyl-N-[(2-hydroxy-3-O-cyanophenoxy)propyl]urea (VI) at 200 C in tetralin. 5) By condensation of the 1-(2-cyanophenoxy)-2,3-epoxypropane (II) with tert-butylamine (C) in ethanol.

参考文献中间体

合成目标

【1】 Koeppe, H.; et al. (Boehringer Ingelheim GmbH.); ZA 6803783 .
【2】 Castaner, J.; Chatterjee, S.S.; Bunitrolol. Drugs Fut 1976, 1, 5, 210.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	37567	2-(2-oxiranylmethoxy)benzonitrile		C₁₀H₉NO₂	详情	详情
(V)	60732	N-(tert-butyl)-N-[3-(2-cyanophenoxy)-2-hydroxypropyl]acetamide		C₁₆H₂₂N₂O₃	详情	详情
(VI)	60733	N,N'-di(tert-butyl)-N-[3-(2-cyanophenoxy)-2-hydroxypropyl]urea		C₁₉H₂₉N₃O₃	详情	详情
(C)	17895	2-Amino-2-methylpropane; tert-butylamine; 2-methyl-2-propanamine	75-64-9	C₄H₁₁N	详情	详情

Extended Information