2-Morpholinoethylamine → N,N-diethyl-4-{[2-(4-morpholinyl)ethyl]amino}-3-nitrobenzamide

HRID 1796449Notes

Reaction equation

HRID 1796449 reaction equation
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2].[N:18]1([CH2:24][CH2:25][NH2:26])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>CCO>[CH2:1]([N:3]([CH2:16][CH3:17])[C:4](=[O:15])[C:5]1[CH:10]=[CH:9][C:8]([NH:26][CH2:25][CH2:24][N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 22181444N,N-diethyl-4-fluoro-3-nitrobenzamide

Product 1

HCID 22181356N,N-diethyl-4-{[2-(4-morpholinyl)ethyl]amino}-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N,N-diethyl-4-fluoro-3-nitrobenzamide (1.00 g, 4.16 mmol), 2-(4-morpholinyl)ethanamine (0.600 mL, 4.58 mmol) in 80% aq. EtOH (50 mL) was refluxed for 4 hours. The reaction was then concentrated in vacuo, and the residue was taken up into EtOAc (40 mL). The organic phase was washed with saturated NaHCO3 (2×10 mL), and the combined aqueous phases were extracted with additional EtOAc (2×20 mL). The combined organic phases were dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound. The crude product was purified by silica gel column chromatography (100% EtOAc to 5% triethylamine/EtOAc) to provide the title compound (1.12 g, 77%) as a bright yellow solid. 1H-NMR (CDCl3): δ 8.67 (s, 1H), 8.28 (d, J=1.2 Hz, 1H), 7.56 (dd, J=8.8 Hz, J=1.6 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 3.77 (t, J=5.2 Hz, 4H), 3.55–3.20 (br m, 6H), 2.74 (t, J=6.4 Hz, 2H), 2.53 (br s, 4H), 1.22 (t, J=6.8 Hz, 6H). MS (ESI) (M+H)+=351.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThe reaction was then concentrated in vacuo
  3. washThe organic phase was washed with saturated NaHCO3 (2×10 mL)
  4. extractionthe combined aqueous phases were extracted with additional EtOAc (2×20 mL)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a9e0eb6c3aac469381a89c033a10bd0e
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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