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【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.

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
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