N-(1,3-dimethoxypropan-2-yl)-N-methyl-4-nitrobenzylamine → 4-((N-(1,3-dimethoxypropan-2-yl)-N-methylamino)methyl)aniline

HRID 566136Notes

Reaction equation

HRID 566136 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:8]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][CH:12]=1)[CH3:9])[CH2:5][O:6][CH3:7]>C(O)(=O)C>[CH3:7][O:6][CH2:5][CH:4]([N:8]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=1)[CH3:9])[CH2:3][O:2][CH3:1]

Participants

3

Reactant 1

HCID 18472590N-(1,3-dimethoxypropan-2-yl)-N-methyl-4-nitrobenzylamine

Product 1

HCID 184723244-((N-(1,3-dimethoxypropan-2-yl)-N-methylamino)methyl)anilineYield 87.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In acetic acid (100 ml) was dissolved N-(1,3-dimethoxypropan-2-yl)-N-methyl-4-nitrobenzylamine (3.1 g), and to the mixture was added reduced iron (3.2 g) little by little. The mixture was stirred at room temperature overnight, and the solvent was evaporated. To the residue was added ethyl acetate, and precipitates were filtered off. The filtrate was washed with sodium hydroxide solution, water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue dissolved in ethyl acetate. To the mixture was added 4N hydrochloric acid-ethyl acetate, and precipitates were filtered and washed with diethylether. The mixture was dissolved in water, and the mixture was neutralized with 1N sodium hydroxide solution and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 4-((N-(1,3-dimethoxypropan-2-yl)-N-methylamino)methyl)aniline (2.4 g) as red oil.

Workup

  1. customthe solvent was evaporated
  2. additionTo the residue was added ethyl acetate
  3. customprecipitates
  4. filtrationwere filtered off
  5. washThe filtrate was washed with sodium hydroxide solution, water and saturated brine
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customUnder reduced pressure, the solvent was evaporated
  8. dissolutionthe residue dissolved in ethyl acetate
  9. additionTo the mixture was added 4N hydrochloric acid-ethyl acetate
  10. customprecipitates
  11. filtrationwere filtered
  12. washwashed with diethylether
  13. dissolutionThe mixture was dissolved in water
  14. extractionextracted with ethyl acetate
  15. washThe organic layer was washed with water and saturated brine
  16. dry with materialdried with anhydrous magnesium sulfate
  17. customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record
ord-0f4ca67927b14c5fabcdfa68f2797e0d
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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