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

HRID 640988ノート

反応式

HRID 640988 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-27466a72c83c4cf282ef0ff321dd02c1
出典データセット
uspto-grants-2010_04
特許番号
US07692005B2

反応ノート

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