Hydrazine hydrate (1:1) → N-(2-aminoethyl)-N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amine

HRID 2273616Notes

Reaction equation

HRID 2273616 reaction equation
[CH2:1]([N:3]([CH2:14][CH2:15][N:16]1C(=O)C2=CC=CC=C2C1=O)[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2].O.NN>C(O)C>[NH2:16][CH2:15][CH2:14][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][O:6][C:7]1[C:8]([F:13])=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 52951945N-[2-[N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amino]ethyl]phthalimide

Product 1

HCID 45258965N-(2-aminoethyl)-N-ethyl-N-[2-(2-fluoropyridin-3-yloxy)ethyl]amineYield 99.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of compound 4 (1.50 g, 4.20 mmol) in ethanol (135 mL) was added hydrazine monohydrate (2.04 mL, 42.0 mmol). The mixture was stirred at room temperature for 14 h. The precipitate was filtered and then washed with ethanol (2×10 mL). The filtrate was evaporated under vacuum and the residue was chromatographed (Al2O3, CH2Cl2/EtOH, 9/1, v/v) to give compound 5 (949 mg, 4.18 mmol) as a yellow oil. Yield 99%; Rf (Al2O3, CH2Cl2/EtOH, 9/1, v/v) 0.36; IR (CCl4) ν 1120, 1190, 1250, 1283, 1453, 1466, 2700-3000 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.08 (t, 3H, J=7.1 Hz), 1.54 (se, 2H), 2.67 (m, 6H), 2.94 (t, 2H, J=6.0 Hz), 4.12 (t, 2H, J=6.0 Hz), 7.13 (ddd, 1H, 5JH-F=0.9 Hz, J=4.8, 7.9 Hz), 7.32 (ddd, 1H, 4JH-F=10.1 Hz, J=1.6, 7.9 Hz), 7.76 (td, 1H, 4JH-F=1.6 Hz, J=1.6, 4.8 Hz); ESI-MS m/z 227.9 [M+H]+.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with ethanol (2×10 mL)
  3. customThe filtrate was evaporated under vacuum
  4. customthe residue was chromatographed (Al2O3, CH2Cl2/EtOH, 9/1

Sources & evidence

ORD record
ord-d93b14533950433b8c412506dd4d6dbc
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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