1-[(1R)-6-methoxy-2,3-dihydro-1H-inden-1-yl]piperazine; methyl (3R)-3-(1-piperazinyl)-2,3-dihydro-1H-inden-5-yl ether -Drug Synthesis Database

【结构式】

【分子编号】64354

【品名】1-[(1R)-6-methoxy-2,3-dihydro-1H-inden-1-yl]piperazine; methyl (3R)-3-(1-piperazinyl)-2,3-dihydro-1H-inden-5-yl ether

【CA登记号】

【分子式】C₁₄H₂₀N₂O

【分子量】232.32568

【元素组成】C 72.38% H 8.68% N 12.06% O 6.89%

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：(IV)

Reductive amination of 6-methoxy-1-indanone (I) with piperazine (II) in the presence of titanium isopropoxide and NaBH4 furnishes the indanyl piperazine (III). Racemic amine (III) is then resolved employing (S)-10-camphorsulfonic acid to provide the (R)-enantiomer (IV). Condensation of the optically active piperazine (IV) with ethyl isocyanate then affords the target urea (1-3).

参考文献中间体

合成目标

【1】 Mattson, R.J.; Catt, J.D.; Keavy, D.; Sloan, C.P.; Epperson, J.; Gao, Q.; Hodges, D.B.; Iben, L.; Mahle, C.D.; Ryan, E.; Yocca, F.D.; Indanyl piperazines as melatonergic MT2 selective agents. Bioorg Med Chem Lett 2003, 13, 6, 1199.
【2】 Mattson, R.J.; Sloan, C.P.; Catt, J.D. (Bristol-Myers Squibb Co.); Novel melatonergic indanyl piperazines or homopiperazines. CA 2175395; EP 0745597 .
【3】 Mattson, R.J.; Catt, J.D. (Bristol-Myers Squibb Co.); Melatonergic indanyl piperazines. US 5780470 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	64586	1-nitrosoethane		C₂H₅NO	详情	详情
(I)	34514	6-methoxy-1-indanone	13623-25-1	C₁₀H₁₀O₂	详情	详情
(II)	10355	Diethylenediamine; Piperazine	110-85-0	C₄H₁₀N₂	详情	详情
(III)	64353	1-(6-methoxy-2,3-dihydro-1H-inden-1-yl)piperazine; methyl 3-(1-piperazinyl)-2,3-dihydro-1H-inden-5-yl ether		C₁₄H₂₀N₂O	详情	详情
(IV)	64354	1-[(1R)-6-methoxy-2,3-dihydro-1H-inden-1-yl]piperazine; methyl (3R)-3-(1-piperazinyl)-2,3-dihydro-1H-inden-5-yl ether		C₁₄H₂₀N₂O	详情	详情

Extended Information