N-[3-(dimethylamino)propyl]-N-methylamine -Drug Synthesis Database

【结构式】

【分子编号】28165

【品名】N-[3-(dimethylamino)propyl]-N-methylamine

【CA登记号】4543-96-8

【分子式】C₆H₁₆N₂

【分子量】116.20652

【元素组成】C 62.02% H 13.88% N 24.11%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(III)

The 5-methylsalicylaldehyde (I) is prepared by a tin (IV) chloride-catalyzed formylation. Iodination of the aldehyde with ICl in glacial acetic acid gives good yield of 3-methyl-5-iodobenzylaldehyde (III). The iodinated salicylaldehyde is reductively aminated with N,N,N'-trimethylpropane-1,3-diamine and sodium borohydride to give N,N,N'-trimethyl-N'-(2-hydroxy-3-methyl-5-iodobenzyl)-1,3-propanediamine (HIPDM) (III) in excellent yield.

参考文献中间体

合成目标

【1】 Blau, M.; Tramposch, K.M.; Kung, H.F.; Radioiodine-labeled N,N-dimethyl-N'-(2-hydroxy-3-ankyl-5-iodobenzyl)-1,3.propanediamines for Brain Perfusion Imaging. J Med Chem 1983, 28, 2, 121-125.
【2】 Kung, H.F.; Hostyniak, P.J.; HIPDM. Drugs Fut 1985, 10, 9, 742.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	10010	o-Cresol	95-48-7	C₇H₈O	详情	详情
(I)	28163	2-hydroxy-3-methylbenzaldehyde		C₈H₈O₂	详情	详情
(II)	28164	2-hydroxy-5-iodo-3-methylbenzaldehyde		C₈H₇IO₂	详情	详情
(III)	28165	N-[3-(dimethylamino)propyl]-N-methylamine	4543-96-8	C₆H₁₆N₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(IV)

The precursor triamine (VI) is prepared as follows. Ethanolamine (I) is protected as the N-Cbz derivative (II) upon treatment with N-(benzyloxycarbonyloxy)succinimide. Subsequent tosylation of (II) to yield (III), followed by displacement of the tosylate of (III) with trimethyl propanediamine (IV) furnishes the protected triamine (V). Then, Cbz group hydrogenolysis in (V) in the presence of Pd/C gives rise to triamine (VI).

参考文献中间体

合成目标

【1】 Dziadulewicz, E.K.; et al.; Nonpeptide bradykinin B2 receptor antagonists: Conversion of rodent-selective bradyzide analogues into potent, orally-active human bradykinin B2 receptor antagonists. J Med Chem 2002, 45, 11, 2160.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(A)	30663	N-benzyloxycarbonyloxysuccinimide; 1-[[(Benzyloxy)carbonyl]oxy]-2,5-pyrrolidinedione	13139-17-8	C₁₂H₁₁NO₅	详情	详情
(I)	10259	Ethanol amine;Ethanolamine;2-Aminoethanol; 2-Amino-1-ethanol；2-Aminoethyl alcohol	141-43-5	C₂H₇NO	详情	详情
(II)	32497	benzyl 2-hydroxyethylcarbamate	77987-49-6	C₁₀H₁₃NO₃	详情	详情
(III)	42170	2-[[(benzyloxy)carbonyl]amino]ethyl 4-methylbenzenesulfonate		C₁₇H₁₉NO₅S	详情	详情
(IV)	28165	N-[3-(dimethylamino)propyl]-N-methylamine	4543-96-8	C₆H₁₆N₂	详情	详情
(V)	61665	benzyl 2-[[3-(dimethylamino)propyl](methyl)amino]ethylcarbamate		C₁₆H₂₇N₃O₂	详情	详情
(VI)	61664	N~1~-(2-aminoethyl)-N~1~,N~3~,N~3~-trimethyl-1,3-propanediamine		C₈H₂₁N₃	详情	详情

Extended Information