N-methyl(2-nitrophenyl)methanamine; N-methyl-N-(2-nitrobenzyl)amine -Drug Synthesis Database

【结构式】

【分子编号】15242

【品名】N-methyl(2-nitrophenyl)methanamine; N-methyl-N-(2-nitrobenzyl)amine

【CA登记号】

【分子式】C₈H₁₀N₂O₂

【分子量】166.17968

【元素组成】C 57.82% H 6.07% N 16.86% O 19.26%

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：(I)

Two related methods have been described: The alkylation of 2-nitrobenzylmethylamine (I) with p-chlorphenyloxyran (II) in boiling ethanol affords N-(2-nitrobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (III), which is further reduced via NaBH4/NiCl2 in boiling methanol to N-(2-aminobenzyl)-2-(methylamino)-1-(4-chlorphenyl)-1-ethanol (IV). The acylation of (IV) with ethyl chloroformate in the presence of pyridine and in a medium of benzene - DMFA (Method A) results in N-[2-(ethoxycarbonyl)amino]-2-(methylamino)-1-(4-chlorophenyl)-1-ethanol (V). The latter is cyclodehydrated by means of conc.H2SO4 in dichloroethane. According to method B, the amino alcohol (IV) is cyclodehydrated by conc.H2SO4 to 8-amino-4-(4-chlorophenyl)-2-methyl-1,2,3-4-tetrahydroisoquinoline (VI), which is acylated with ethyl chloroformate in boiling benzene.

参考文献中间体

合成目标

【1】 Ivanova, N.; Ivanov, T.; Mondeshka, D.; Berova, N.; Angelova, I.; Rakovska, R.; Bojadjiev, S.; Tancheva, C.; Tascheva, D.; Synthesis, stereochemistry, and antiulcer activity of 4-phenyltetrahydroisoquinolines. Arch Pharm 1990, 323, 1, 3.
【2】 Ivanova, N.; Angelova, J.; Mondeshka, D.; Ivanov, C.; Gastrophenzine. Drugs Fut 1992, 17, 2, 104.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	15242	N-methyl(2-nitrophenyl)methanamine; N-methyl-N-(2-nitrobenzyl)amine	C₈H₁₀N₂O₂	详情	详情
(II)	15243	2-(4-chlorophenyl)oxirane	C₈H₇ClO	详情	详情
(III)	15244	1-(4-chlorophenyl)-2-[methyl(2-nitrobenzyl)amino]-1-ethanol	C₁₆H₁₇ClN₂O₃	详情	详情
(IV)	15245	2-[(2-aminobenzyl)(methyl)amino]-1-(4-chlorophenyl)-1-ethanol	C₁₆H₁₉ClN₂O	详情	详情
(V)	15246	ethyl N-(2-[[[2-(4-chlorophenyl)-2-hydroxyethyl](methyl)amino]methyl]phenyl)carbamate	C₁₉H₂₃ClN₂O₃	详情	详情
(VI)	15247	4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydro-8-isoquinolinamine; 4-(4-chlorophenyl)-2-methyl-1,2,3,4-tetrahydro-8-isoquinolinylamine	C₁₆H₁₇ClN₂	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

By condensation of 2-nitrobenzylmethylamine (I) with alpha-bromoacetophenone (A) in ethanol to give omega-[N-(2-nitrobenzyl)methylamino]acetophenone (II) (HCl salt, m.p. 165-7 C), which is then reduced first with H2 over Pd/C, or Ni-diatomaceous earth and afterwards with NaBH4 in CH2Cl2 to give N-(2-aminobenzyl)-1-phenyl-2-methylaminoethanol (III), m.p. 67-9 C. This product is finally cyclized with sulfuric acid.

参考文献中间体

合成目标

【1】 Chatterjee, S.S.; Castañer, J.; Nomifensin. Drugs Fut 1976, 1, 2, 72.
【2】 Hoffmann, I.; Gustav, E.; Schmitt, K.; 8-Amino-4-phenyl-1,2,3,4-tetrahydroisoquinolines, a new group of anti-depressive psycholeptic drugs. Arzneim-Forsch Drug Res 1971, 21, 7, 1045.
【3】 Hoffmann, I.; Gustav, E.; Heinrich, O.; Schmitt, K. (Aventis Pharma AG); 4-Phenyl-8-amino tetrahydroisoquinolines. DE 1670694; DE 1670848; FR 1524487; FR 6496M; FR 6646M; GB 1164192; US 3577424 .

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)	10315	2-Bromo-1-phenyl-ethanone; 2-Bromo-1-phenyl-1-ethanone	70-11-1	C₈H₇BrO	详情	详情
(I)	15242	N-methyl(2-nitrophenyl)methanamine; N-methyl-N-(2-nitrobenzyl)amine		C₈H₁₀N₂O₂	详情	详情
(II)	40345	2-[methyl(2-nitrobenzyl)amino]-1-phenyl-1-ethanone		C₁₆H₁₆N₂O₃	详情	详情
(III)	40346	2-[(2-aminobenzyl)(methyl)amino]-1-phenyl-1-ethanol		C₁₆H₂₀N₂O	详情	详情

Extended Information