N,N-Dimethylethylenediamine → 4-[[2-(Dimethylamino)ethyl]amino]-N,N-diethyl-3-nitrobenzamide

HRID 1796467Notes

Reaction equation

HRID 1796467 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].[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH2:22]>>[CH3:18][N:19]([CH3:23])[CH2:20][CH2:21][NH:22][C:8]1[CH:9]=[CH:10][C:5]([C:4]([N:3]([CH2:16][CH3:17])[CH2:1][CH3:2])=[O:15])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13]

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 22181444N,N-diethyl-4-fluoro-3-nitrobenzamide

Product 1

HCID 221813844-[[2-(Dimethylamino)ethyl]amino]-N,N-diethyl-3-nitrobenzamideYield 89.9%

Conditions

Temperature
85 °C

Procedure

Following general procedure 2B, N,N-diethyl-4-fluoro-3-nitrobenzamide (0.534 g, 2.22 mmol) and N1,N1-dimethyl-1,2-ethanediamine (0.22 mL, 2.02 mmol) were stirred at 85° C. for 14 h. The crude product was purified through dissolution in 1 N HCl and extraction with Et2O (2×15 mL). The aqueous phase was adjusted to pH 11 with 5 N NaOH and then extracted with CH2Cl2 (4×15 mL). The combined CH2Cl2 phases were dried over MgSO4, filtered, and concentrated in vacuo to provide the title compound (0.560 g, 82%) as an orange oil. 1H-NMR (CD3OD): δ 8.22 (d, J=2.8 Hz, 1H), 7.56 (dd, J=8.4 Hz, J=2.8 Hz, 1H), 7.09 (d, J=8.4 Hz, 1H), 3.53–3.40 (overlapping t, J=6.4 Hz, and br s, 6H), 2.67 (t, J=6.4 Hz, 2H), 2.33 (s, 6H), 1.22 (t, J=7.6 Hz, 6H). MS (ESI) (M+H)+=309

Workup

  1. customThe crude product was purified through dissolution in 1 N HCl
  2. extractionextraction with Et2O (2×15 mL)
  3. extractionextracted with CH2Cl2 (4×15 mL)
  4. dry with materialThe combined CH2Cl2 phases were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6eb8e268a26543f6ba0268e1ac8dc02c
Source dataset
uspto-grants-2006_04
Patent number
US07030139B2

Reaction notes

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