5-(3-bromopropylidene)-5H-dibenzo[a,d]cycloheptene -Drug Synthesis Database

【结构式】

【分子编号】40130

【品名】5-(3-bromopropylidene)-5H-dibenzo[a,d]cycloheptene

【CA登记号】

【分子式】C₁₈H₁₅Br

【分子量】311.2211

【元素组成】C 69.47% H 4.86% Br 25.67%

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)

The Grignard reaction of dibenzo[a,d]cyclohepta-1,4,6-triene-5-one (I) with cyclopropyl magnesium bromide (D) in THF gives 5-hydroxy-5-cyclopropyldibenzo[a,d]cyclohepta-1,4,6-triene (V), which is then treated with HBr in acetic acid to yield 5-(3-bromopropylidene)dibenzo[a,d]cyclohepta-1,4,6-triene (VI). Finally, (VI) is treated with dimethylamine (B) in benzene at 95 C. The hydroxycompound (V), obtained as before, is treated with HClO4 in dioxane to yield 5-(3-hydroxypropylidene)dibenzo[a,d]cyclohepta-1,4,6-triene (VII), which is then treated with p-toluenesulfonyl chloride in pyridine to afford the tosyl derivate (VIII). Finally, (VIII) is treated with dimethylamine (B) in benzene at 100 C.

参考文献中间体

合成目标

【1】 Roberts, P.J.; Castañer, J.; Cyclobenzaprine. Drugs Fut 1977, 2, 5, 299.
【2】 Hoffsommer, R.D. Jr.; et al.; Nouveaux derives de dibenzocycloheptenes et leur preparation. BE 0631012 .
【3】 Wendler, N.L.; Dibenzocycloheptenes. BE 0633316 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(D)	12450	Bromo(cyclopropyl)magnesium;cyclopropylmagnesium bromide;cyclopropylmagnesiumbromide	23719-80-4	C₃H₅BrMg	详情	详情
(B)	19443	N-methylmethanamine; N,N-dimethylamine	124-40-3	C₂H₇N	详情	详情
(I)	29151	5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberenone	2222-33-5	C₁₅H₁₀O	详情	详情
(V)	40129	5-cyclopropyl-5H-dibenzo[a,d]cyclohepten-5-ol		C₁₈H₁₆O	详情	详情
(VI)	40130	5-(3-bromopropylidene)-5H-dibenzo[a,d]cycloheptene		C₁₈H₁₅Br	详情	详情
(VII)	40131	3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propanol		C₁₈H₁₆O	详情	详情
(VIII)	40132	3-(5H-dibenzo[a,d]cyclohepten-5-ylidene)propyl 4-methylbenzenesulfonate		C₂₅H₂₂O₃S	详情	详情

Extended Information