N-[2-[N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amino]ethyl]phthalimide → N-(2-aminoethyl)-N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amine

HRID 2273641Notes

Reaction equation

HRID 2273641 reaction equation
[CH2:1]([N:3]([CH2:16][CH2:17][N:18]1C(=O)C2=CC=CC=C2C1=O)[CH2:4][CH2:5][O:6][C:7]1[C:8]([N+:13]([O-:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].NCCN(CC)CCF>>[NH2:18][CH2:17][CH2:16][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[C:8]([N+:13]([O-:15])=[O:14])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

3

Reactant 2

HCID 52952579N-[2-[N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amino]ethyl]phthalimideHCID 55285943N-(2-aminoethyl)-N-ethyl-N-(2-fluoroethyl)amine

Product 1

HCID 52952580N-(2-aminoethyl)-N-ethyl-N-[2-(2-nitropyridin-3-yloxy)ethyl]amineYield 77%

Procedure

This compound was prepared, starting from compound 58 (2.00 g, 5.20 mmol), according to the procedure developed for compound 22. Reaction time under reflux: 12 h; the purification was performed using column chromatography (Al2O3, CH2Cl2/EtOH, 95/5, v/v) to give compound 59 (1.01 g, 3.97 mmol) as a yellow oil. Yield 77%; Rf (Al2O3, CH2Cl2/EtOH, 95/5, v/v) 0.36; 1H NMR (200 MHz, CDCl3) δ 1.11 (t, 3H, J=7.1 Hz), 2.72 (m, 8H), 2.99 (t, 2H, J=5.6 Hz), 4.28 (t, 2H, J=5.6 Hz), 7.63 (dd, 1H, J=4.3, 8.4 Hz), 7.71 (dd, 1H, J=1.5, 8.4 Hz), 8.13 (dd, 1H, J=1.5, 4.3 Hz); ESI-MS m/z 255.0 [M+H]+.

Workup

  1. customThis compound was prepared
  2. customReaction time
  3. temperatureunder reflux
  4. custom12 h
  5. customthe purification

Sources & evidence

ORD record
ord-d274913ac6a2448383a6dde05a902ca9
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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