Potassium Carbonate → 1-[2-(N,N-dimethylamino)-4-nitrophenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane

HRID 1106882Notes

Reaction equation

HRID 1106882 reaction equation
Cl[CH2:2][CH2:3][N:4]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[CH3:5].[CH3:18][N:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[OH:30])[CH3:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(=O)(O)[O-].[Na+]>[CH3:20][N:19]([C:21]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:22]=1[O:30][CH2:2][CH2:3][N:4]([CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)[CH3:5])[CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 136051471-chloro-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethaneHCID 187899052-(N,N-dimethylamino)-4-nitrophenol

Product 1

HCID 187898891-[2-(N,N-dimethylamino)-4-nitrophenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethaneYield 55.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A portion (1 g, 3.88 mmol) of the 1-chloro-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane produced in (1) above, 2-(N,N-dimethylamino)-4-nitrophenol (0.598 g, 3.88 mmol) and potassium carbonate (0.536 g, 3.88 mmol) were heated in dimethylformamide (10 ml) at 80° C. for 2 h. Thereafter, the reaction mixture was diluted with a saturated solution of sodium bicarbonate, subjected to extraction with ethyl acetate and dried with anhydrous magnesium sulfate, followed by evaporation of the solvent. The residue was purified by being subjected to column chromatography on silica gel using, as an eluent, chloroform containing methanol (5%) to yield the titled compound 1-[2-(N,N-dimethylamino)-4-nitrophenoxy]-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (0.87 g) as a foam.

Workup

  1. extractionsubjected to extraction with ethyl acetate
  2. dry with materialdried with anhydrous magnesium sulfate
  3. customfollowed by evaporation of the solvent
  4. customThe residue was purified
  5. additionchloroform containing methanol (5%)

Sources & evidence

ORD record
ord-29c84e0e96ec45e590972983251fbe69
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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