1-Pyrrolidineethanamine → 4-Nitro-N-[2-(pyrrolidin-1-yl)ethyl]aniline

HRID 640988노트

반응식

HRID 640988 반응식
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[N:11]1([CH2:16][CH2:17][NH2:18])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(N)C>O1CCOCC1>[N+:8]([C:3]1[CH:4]=[CH:5][C:6]([NH:18][CH2:17][CH2:16][N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:7][CH:2]=1)([O-:10])=[O:9]

참가 물질

5

반응물 3

HCID 13441-PyrrolidineethanamineHCID 6341EthylamineHCID 738951-Fluoro-2-nitrobenzene

생성물 1

HCID 585989084-Nitro-N-[2-(pyrrolidin-1-yl)ethyl]aniline수율 85%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A 50 mL round bottom flask was dried in an oven overnight and cooled to room temperature under Ar(g). The flask was charged with fluoronitrobenzene (0.187 mL, 1.77 mmol), 2-Pyrrolidin-1-yl-ethylamine (0.201 g, 2.30 mmol) and dioxane (9.0 mL). To the solution, diispropyl ethyl amine (0.463 mL, 2.66 mmol) was added dropwise and allowed to stir at 105° C. for 48 h. The mixture was extracted with EtOAc (3ט30 mL), and with brine (2ט30 mL). The combined organic layers were then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude mixture was then purified over silica (10% MeOH/90% CHCl3) affording (4-Nitro-phenyl)-(2-pyrrolidin-1-yl-ethyl)-amine as a yellow solid (0.352 g, 1.50 mmol, 85% yield).

후처리

  1. customA 50 mL round bottom flask was dried in an oven overnight
  2. extractionThe mixture was extracted with EtOAc (3ט30 mL)
  3. dry with materialThe combined organic layers were then dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude mixture was then purified over silica (10% MeOH/90% CHCl3)

출처 및 근거

ORD 기록
ord-27466a72c83c4cf282ef0ff321dd02c1
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07692005B2

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