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

HRID 640988Notes

Reaction equation

HRID 640988 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-27466a72c83c4cf282ef0ff321dd02c1
Source dataset
uspto-grants-2010_04
Patent number
US07692005B2

Reaction notes

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