Bevantolol hydrochloride, Bevantol hydrochloride, NC-1400, CI-775, Calvan, Vantol, Ranestol, -Drug Synthesis Database

【结构式】

【药物名称】Bevantolol hydrochloride, Bevantol hydrochloride, NC-1400, CI-775, Calvan, Vantol, Ranestol

【化学名称】(±)-1-[[2-(3,4-Dimethoxyphenyl)ethyl]amino]-3-(3-methylphenoxy)-2-propanol hydrochloride

【CA登记号】42864-78-8, 59170-23-9 (free base)

【分子式】C₂₀H₂₈ClNO₄

【分子量】381.90346

【开发单位】Pfizer (Originator), Nippon Chemiphar (Licensee), Ube (Licensee)

【药理作用】CARDIOVASCULAR DRUGS, Hypertension, Treatment of, beta-Adrenoceptor Antagonists

合成路线1 合成路线2

合成路线1

The condensation of 3-methylphenol (I) and epichlorohydrin (II) by means of NaOH gives 1,2-epoxy-3-(3-methylphenoxy)propane (III), which is then condensed with 3,4-dimethoxyphenylethylamine (V) by heating their mixture at 95-100 C.

参考文献中间体

【1】 Holmes, A.; Meyer, R.F.; New aminoalkanol compounds and methods for their production. FR 2163486; GB 1344976; JP 48067232 .
【2】 Milton, L.H.; et al.; Cardioselective beta-adrenergic blocking agents. 1. 1-[3,4-(dimethoxyphenethyl)amino]-3-aryloxy-2-propanols. J Med Chem 1975, 18, 2, 148-152.
【3】 Castaner, J.; Weetman, D.F.; Bevantol. Drugs Fut 1977, 2, 8, 500.

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)	17793	m-cresol; m-Methylphenol	108-39-4	C₇H₈O	详情	详情
(II)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(III)	33968	2-[(3-methylphenoxy)methyl]oxirane; 3-methylphenyl 2-oxiranylmethyl ether		C₁₀H₁₂O₂	详情	详情
(V)	10098	2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine	120-20-7	C₁₀H₁₅NO₂	详情	详情

合成路线2

The condensation of 3-methylphenol (I) with epichlorohydrin (II) by means of a catalytic amount of piperidine gives 1-(3-methylphenoxy)-3-chloro-2-propanol (IV), which is then condensed with 3,4-dimethoxyphenylethylamine (V) by heating their mixture at 95-100 C.

参考文献中间体

【1】 Holmes, A.; Meyer, R.F.; New aminoalkanol compounds and methods for their production. FR 2163486; GB 1344976; JP 48067232 .
【2】 Milton, L.H.; et al.; Cardioselective beta-adrenergic blocking agents. 1. 1-[3,4-(dimethoxyphenethyl)amino]-3-aryloxy-2-propanols. J Med Chem 1975, 18, 2, 148-152.
【3】 Castaner, J.; Weetman, D.F.; Bevantol. Drugs Fut 1977, 2, 8, 500.

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)	17793	m-cresol; m-Methylphenol	108-39-4	C₇H₈O	详情	详情
(II)	10146	Epichlorohydrin; 2-(Chloromethyl)oxirane	106-89-8	C₃H₅ClO	详情	详情
(IV)	33967	1-chloro-3-(3-methylphenoxy)-2-propanol		C₁₀H₁₃ClO₂	详情	详情
(V)	10098	2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine	120-20-7	C₁₀H₁₅NO₂	详情	详情

Extended Information