Water → HCID 18789888, compound

HRID 1106865Notes

Reaction equation

HRID 1106865 reaction equation
[Cl:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][CH2:5][CH2:6][N:7]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=1)[CH3:8].[O-]S(S([O-])=O)=O.[Na+].[Na+].O>C(O)C>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][CH2:5][CH2:6][N:7]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH3:20])[CH:12]=2)[CH3:8])=[C:2]([Cl:1])[CH:24]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 18789961HCID 18789961, compound

Product 1

HCID 18789888HCID 18789888, compoundYield 32.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A portion (15.63 g, 0.040 mol) of the 1-(2-chloro-4-nitrophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane produced in (2) above was dissolved in hot ethanol (500 ml) and, thereafter, a solution consisting of a mixture of Na2S2O4 (27.56 g) and water (125 ml) was added to the resulting solution, thereby forming a precipitate. The mixture was heated at the reflux temperature for 20 min. Thereafter, the solvent was evaporated and the residue was diluted with water, followed by extraction with ethyl acetate. An aqueous solution of sodium carbonate was added to the aqueous layer such that it became basic up to a pH of about 9, followed by three extractions with ethyl acetate. The organic extracts were combined, dried with magnesium sulfate, and the solvent was evaporated; thereafter, the residue was purified by being subjected to column chromatography on silica gel using, as an eluent, ethyl acetate containing methanol (10%). The fractions containing the end compound were combined and the solvent was evaporated to yield the end compound 1-(4-amino-2-chlorophenoxy)-2-[N-(3,4-dimethoxyphenethyl)-N-methylamino]ethane (4.78 g) as a yellow oil.

Workup

  1. additionwas added to the resulting solution
  2. customforming a precipitate
  3. temperatureThe mixture was heated at the reflux temperature for 20 min
  4. customThereafter, the solvent was evaporated
  5. additionthe residue was diluted with water
  6. extractionfollowed by extraction with ethyl acetate
  7. additionAn aqueous solution of sodium carbonate was added to the aqueous layer such that it
  8. extractionfollowed by three extractions with ethyl acetate
  9. dry with materialdried with magnesium sulfate
  10. customthe solvent was evaporated
  11. customthereafter, the residue was purified
  12. additionethyl acetate containing methanol (10%)
  13. additionThe fractions containing the end compound
  14. customthe solvent was evaporated

Sources & evidence

ORD record
ord-54cf0c52b8814b3fbdae53c9e0c9c477
Source dataset
uspto-grants-2000_05
Patent number
US06057358

Reaction notes

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