2-[methyl(2-nitrobenzyl)amino]-1-phenyl-1-ethanone -Drug Synthesis Database

【结构式】

【分子编号】40345

【品名】2-[methyl(2-nitrobenzyl)amino]-1-phenyl-1-ethanone

【CA登记号】

【分子式】C₁₆H₁₆N₂O₃

【分子量】284.31472

【元素组成】C 67.59% H 5.67% N 9.85% O 16.88%

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：(II)

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