5H-dibenzo[a,d]cyclohepten-5-one oxime -Drug Synthesis Database

【结构式】

【分子编号】31713

【品名】5H-dibenzo[a,d]cyclohepten-5-one oxime

【CA登记号】

【分子式】C₁₅H₁₁NO

【分子量】221.25848

【元素组成】C 81.43% H 5.01% N 6.33% O 7.23%

与该中间体有关的原料药合成路线共 3 条

合成路线1 合成路线2 合成路线3

合成路线1

该中间体在本合成路线中的序号：(I)

By reaction of 5H-dibenzo[a,d]cyclohepten-5-one oxime (I) with beta-methylaminoethyl chloride (II) in a solution of sodium in methanol.

参考文献中间体

合成目标

【1】 Behner, O.; Aichinger, G.; Hoffmeister, F.; Schuetz, S.; Basic tricyclic oximino ether and their pharmacological properties. Arzneim-Forsch Drug Res 1969, 19, 5a, 838-845.
【2】 Schuetz, S.; Behner, O.; Hoffmeister, F. (Bayer AG); Basic oximes and their preparation. DE 1247302; FR 1500629; GB 1104609; US 3963778; US 3989844 .
【3】 Castaner, J.; Serradell, M.N.; Blancafort, P.; Demexiptiline hydrochloride. Drugs Fut 1982, 7, 1, 19.

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)	31713	5H-dibenzo[a,d]cyclohepten-5-one oxime		C₁₅H₁₁NO	详情	详情
(II)	31714	2-chloro-N-methyl-1-ethanamine; N-(2-chloroethyl)-N-methylamine		C₃H₈ClN	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

By decomposition of O-beta-(N-methyl-N-carbethoxy)aminoethyl-5H-dibenzo[a,d]cyclohepten-5-one oxime (III) with KOH in carbitol. Compound (III) can be prepared as follows: 5H-ibenzo[a,d]cyclohepten-5-one oxime (I) is treated with beta-dimethylaminoethyl chloride (IV) in sodium methoxide to give O-beta-dimethylaminoethyl-5H-dibenzo[a,d]cyclohepten-5-one oxime (V), which is treated with ethyl chlorocarbonate in anhydrous benzene.

参考文献中间体

合成目标

【1】 Pirola, O.; Rossi, S.; Fanelli, O.; Maggi, R.; O- And N- substituted 5H-dibenzo[a,d]cyclohepten-5-one oximes with thymoleptic acticity. VII. Synthesis and pharmacological properties of the substituted oximes. Farm Sci Ed 1969, 24, 7, 685-703.
【2】 Castaner, J.; Serradell, M.N.; Blancafort, P.; Demexiptiline hydrochloride. Drugs Fut 1982, 7, 1, 19.

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)	31713	5H-dibenzo[a,d]cyclohepten-5-one oxime		C₁₅H₁₁NO	详情	详情
(III)	31716	ethyl 2-[(5H-dibenzo[a,d]cyclohepten-5-ylideneamino)oxy]ethyl(methyl)carbamate		C₂₁H₂₂N₂O₃	详情	详情
(IV)	11907	Dimethylaminoethyl chloride; 2-Dimethylaminoethyl chloride; 2-Chloro-N,N-dimethyl-1-ethanamine; N-(2-Chloroethyl)-N,N-dimethylamine	107-99-3	C₄H₁₀ClN	详情	详情
(V)	31715	5H-dibenzo[a,d]cyclohepten-5-one O-[2-(dimethylamino)ethyl]oxime		C₁₉H₂₀N₂O	详情	详情

合成路线3

该中间体在本合成路线中的序号：(I)

beta-Methylaminoethanol (VI) is treated with ethyl chlorocarbonate in triethylamine to give ethyl N-methyl-hydroxyethylcarbamate (VII), which is treated with thionyl chloride to give ethyl-N-methyl-beta-chloroethylcarbamate (VIII). Compound (VIII) is treated with 5H-dibenzo[a,d]cyclohepten-5-one oxime (I) and the resulting product is decomposed without isolation.

参考文献中间体

合成目标

【1】 Pirola, O.; Rossi, S.; Fanelli, O.; Maggi, R.; O- And N- substituted 5H-dibenzo[a,d]cyclohepten-5-one oximes with thymoleptic acticity. VII. Synthesis and pharmacological properties of the substituted oximes. Farm Sci Ed 1969, 24, 7, 685-703.
【2】 Castaner, J.; Serradell, M.N.; Blancafort, P.; Demexiptiline hydrochloride. Drugs Fut 1982, 7, 1, 19.

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)	31713	5H-dibenzo[a,d]cyclohepten-5-one oxime		C₁₅H₁₁NO	详情	详情
(VI)	13324	2-Methylaminoethanol; 2-(Methylamino)-1-ethanol	109-83-1	C₃H₉NO	详情	详情
(VII)	31717	ethyl 2-hydroxyethyl(methyl)carbamate		C₆H₁₃NO₃	详情	详情
(VIII)	31718	ethyl 2-chloroethyl(methyl)carbamate		C₆H₁₂ClNO₂	详情	详情

Extended Information