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

【结构式】

【分子编号】35932

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

【CA登记号】

【分子式】C₁₅H₁₁N

【分子量】205.25908

【元素组成】C 87.77% H 5.4% N 6.82%

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：(VIII)

The reaction of 5H-dibenzo[a,d]cyclohepten-5-one (VII) with NH3 and TiCl4 in toluene gives 5H-dibenzo[a,d]cycloheptene-5-imine (VIII), which is tosylated with p-toluenesulfonyl chloride in pyridine to yield 5-(p-toluenesulfonimino)-5H-dibenzo[a,d]cycloheptene (IX). The methylation of (IX) with methyllithium in dry THF affords 5-methyl-5-(p-toluenesulfonimido)-5H-dibenzo[a,d]cycloheptene (X), which is internally cyclized by means of KOH in diglyme at 170 C giving 5-methyl-N-(p-toluenesulfonyl)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-5,10-imine (XI). Finally, this compound is hydrolyzed with aqueous HCl in refluxing AcOH.

参考文献中间体

合成目标

【1】 Shepard, K.L.; Brenner, D.G.; EP 0019866 .
【2】 Thorpe, P.J.; Castaner, J.; Serradell, M.N.; Blancafort, P.; MK-801. Drugs Fut 1983, 8, 2, 120.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VII)	29151	5H-dibenzo[a,d]cyclohepten-5-one; Dibenzosuberenone	2222-33-5	C₁₅H₁₀O	详情	详情
(VIII)	35932	5H-dibenzo[a,d]cyclohepten-5-imine		C₁₅H₁₁N	详情	详情
(IX)	35933	N-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-4-methylbenzenesulfonamide		C₂₂H₁₇NO₂S	详情	详情
(X)	35934	4-methyl-N-(5-methyl-5H-dibenzo[a,d]cyclohepten-5-yl)benzenesulfonamide		C₂₃H₂₁NO₂S	详情	详情
(XI)	35935	1-methyl-16-[(4-methylphenyl)sulfonyl]-16-azatetracyclo[7.6.1.0(2,7).0(10,15)]hexadeca-2,4,6,10,12,14-hexaene		C₂₃H₂₁NO₂S	详情	详情

Extended Information