Methyl 4-aminobenzoate → Methyl 4-[N-(5-bromo-2-(phenethyl)benzyl)amino]benzoate

HRID 1006004Notes

Reaction equation

HRID 1006004 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH:9]=1)[CH:7]=O.[NH2:18][C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:6]([CH:9]=1)[CH2:7][NH:18][C:19]1[CH:20]=[CH:21][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 12082Methyl 4-aminobenzoateHCID 226754825-Bromo-2-(phenethyl)benzaldehyde

Product 1

HCID 22675570Methyl 4-[N-(5-bromo-2-(phenethyl)benzyl)amino]benzoateYield 89.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

5-Bromo-2-(phenethyl)benzaldehyde (1.27 g) and methyl 4-aminobenzoate (0.66 g) were heated together at 110° C. for 30 minutes and for a further 30 minutes under vacuum. The mixture was dissolved in toluene, evaporated to dryness, dissolved in ethanol (15 ml). Sodium borohydride (0.33 g) was added, the mixture stirred for 18 hours, the solvent evaporated and the residue mixed with acetic acid and partitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate. The organic layer was washed with brine, dried (MgSO4), filtered and evaporated. The resulting residue was purified by MPLC, eluting with dichloromethane, to give methyl 4-[N-(5-bromo-2-(phenethyl)benzyl)amino]benzoate (1.65 g).

Workup

  1. customevaporated to dryness
  2. dissolutiondissolved in ethanol (15 ml)
  3. additionSodium borohydride (0.33 g) was added
  4. customthe solvent evaporated
  5. additionthe residue mixed with acetic acid
  6. custompartitioned between saturated aqueous sodium hydrogen carbonate and ethyl acetate
  7. washThe organic layer was washed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customThe resulting residue was purified by MPLC
  12. washeluting with dichloromethane

Sources & evidence

ORD record
ord-f4237f4814b44882a9fe6d7bdf572365
Source dataset
uspto-grants-2004_09
Patent number
US06787562B2

Reaction notes

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