Potassium Carbonate → HCID 19915724, compound

HRID 1032673Notes

Reaction equation

HRID 1032673 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9][NH2:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[N+:13]([C:16]1[CH:24]=[CH:23][C:19]([CH2:20][CH2:21]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][CH2:9][NH:10][CH2:21][CH2:20][C:19]2[CH:18]=[CH:17][C:16]([N+:13]([O-:15])=[O:14])=[CH:24][CH:23]=2)=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 792664-Nitrophenethyl bromideHCID 951534-Nitrophenethylamine

Product 1

HCID 19915724HCID 19915724, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Nitrophenethylamine (4 g), 4-nitrophenethyl bromide (5.54 g) and potassium carbonate (3.32 g) were heated under reflux in acetonitrile (50 ml) for 2 days. The solvent was then evaporated, the residue taken up in ethyl acetate and washed three times with aqueous sodium carbonate and three times with brine. The organic phase was dried (Na2SO4), filtered and evaporated, and the residual oil was purified by chromatography on silica eluting with methylene chloride containing methanol (0% up to 5%). The product-containing fractions were combined and the solvent evaporated to give a solid which was recrystallised from ethyl acetate/hexane to give the title compound, yield 2.0 g, m.p. 86°-91°.

Workup

  1. customThe solvent was then evaporated
  2. washwashed three times with aqueous sodium carbonate and three times with brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customthe residual oil was purified by chromatography on silica eluting with methylene chloride
  7. additioncontaining methanol (0% up to 5%)
  8. customthe solvent evaporated
  9. customto give a solid which
  10. customwas recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-6287bf8e0cf342818ca139e4c3a31da0
Source dataset
uspto-grants-1990_09
Patent number
US04959366

Reaction notes

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