Trepipam, Trimopam(formerly), Sch-12679(maleate), -Drug Synthesis Database

【结构式】

【药物名称】Trepipam, Trimopam(formerly), Sch-12679(maleate)

【化学名称】(+)-2,3,4,5-Tetrahydro-7,8-dimethoxy-3-methyl-1-phenyl-1H-3-benzazepine

【CA登记号】56030-50-3, 39624-66-3 (maleate)

【分子式】C₁₉H₂₃NO₂

【分子量】297.40066

【开发单位】Schering-Plough (Originator)

【药理作用】Antipsychotic Drugs, PSYCHOPHARMACOLOGIC DRUGS

合成路线1 合成路线2

合成路线1

By condensation of styrene oxide (I) with 3,4-dimethoxyphenylethylamine (II) at 100 C to give N-(beta-hydroxy-beta-phenyl)ethyl-2-(3',4'-dimethoxyphenyl)ehtylamine (III), which is cyclized with H2SO4 to 1-phenyl-7,8-dimethoxy-2,3,4,5-tetrahydro-3,1-benzazepine (IV). This product is finally methylated with a refluxing mixture of formaldehyde and formic acid.

参考文献中间体

【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.
【2】 Walter, L.A.; Chang, W.K. (Schering Corp.); Novel benzazepines. US 3393192 .
【3】 Castaner, J.; Thorpe, P.; Trimopam. Drugs Fut 1976, 1, 4, 194.

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)	23017	2-phenyloxirane	96-09-3	C₈H₈O	详情	详情
(II)	10098	2-(3,4-Dimethoxyphenyl)-1-ethanamine; 3,4-Dimethoxyphenethylamine; 2-(3,4-Dimethoxyphenyl)ethylamine	120-20-7	C₁₀H₁₅NO₂	详情	详情
(III)	39206	2-[(3,4-dimethoxyphenethyl)amino]-1-phenyl-1-ethanol		C₁₈H₂₃NO₃	详情	详情
(IV)	39207	7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine; 8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin-7-yl methyl ether		C₁₈H₂₁NO₂	详情	详情

合成路线2

The bromination of labeled acetophenone (I) with Br2 and AlCl3 gives phenacyl bromide (II), which is condensed with N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylamine (III), yielding the 2-aminoacetophenone (IV). The reduction of (IV) with NaBH4 affords the secondary alcohol (V), which is finally cyclized by means of H2SO4 and trifluoroacetic acid to provide the target 3-benzazepine.

参考文献中间体

【1】 Hieble, J.P.; Wilson III, J.W.; Weinstock, J.; The chemistry and pharmacology of 3-benzazepines derivatives. Drugs Fut 1985, 10, 8, 645.

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)	10317	Acetophenone	98-86-2	C₈H₈O	详情	详情
(I)	44572	acetophenone		C₈H₈O	详情	详情
(II)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(II)	44573	2-bromo-1-phenyl-1-ethanone		C₈H₇BrO	详情	详情
(III)	18938	2-(3,4-dimethoxyphenyl)-N-methyl-1-ethanamine; N-(3,4-dimethoxyphenethyl)-N-methylamine	3490-06-0	C₁₁H₁₇NO₂	详情	详情
(IV)	44047	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanone		C₁₉H₂₃NO₃	详情	详情
(IV)	44574	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanone		C₁₉H₂₃NO₃	详情	详情
(V)	44048	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanol		C₁₉H₂₅NO₃	详情	详情
(V)	44575	2-[(3,4-dimethoxyphenethyl)(methyl)amino]-1-phenyl-1-ethanol		C₁₉H₂₅NO₃	详情	详情

Extended Information