N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamide → N-(4,6-dimethyl-pyridin-2-yl)-N,N'-dimethyl-N'-(4-nitro-phenyl)-propane-1,3-diamine

HRID 37838Notes

Reaction equation

HRID 37838 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH3:25])[C:10](=O)[CH2:11][CH2:12][N:13]([CH3:23])[C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:3]=1>O1CCCC1>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]([CH3:25])[CH2:10][CH2:11][CH2:12][N:13]([CH3:23])[C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[CH:3]=1

Participants

3

Reactant 1

HCID 66851224N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamide

Product 1

HCID 66851546N-(4,6-dimethyl-pyridin-2-yl)-N,N'-dimethyl-N'-(4-nitro-phenyl)-propane-1,3-diamineYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-dimethylsulfide complex (0.72 mL, 7.02 mmol) was added to a solution of N-(4,6-dimethyl-pyridin-2-yl)-N-methyl-3-[methyl-(4-nitro-phenyl)-amino]-propionamide (600 mg, 1.75 mmol) in tetrahydrofuran (10 mL) at 0° C. The mixture was warmed to room temperature then heated at reflux overnight. After cooling to room temperature the solvent was evaporated in vacuo. The residue was quenched into ice water, extracted with ethyl acetate then the organic phase was washed with water and brine, dried over anhydrous sodium sulfate and concentrated in vacuo. Purification of the residue by column chromatography over silica gel (60-120 mesh) using 10% ethyl acetate in hexane as eluent afforded N-(4,6-dimethyl-pyridin-2-yl)-N,N′-dimethyl-N′-(4-nitro-phenyl)-propane-1,3-diamine (350 mg, 61%) as yellow semi solid.

Workup

  1. temperaturethen heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling to room temperature the solvent
  4. customwas evaporated in vacuo
  5. customThe residue was quenched into ice water
  6. extractionextracted with ethyl acetate
  7. washthe organic phase was washed with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated in vacuo
  10. customPurification of the residue by column chromatography over silica gel (60-120 mesh)

Sources & evidence

ORD record
ord-d1afbfab80f04a2794cc9e562f84a46c
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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