Benzylamine → N-(2-Methoxyphenyl)-2-[(phenylmethyl)amino]acetamide

HRID 1588975Notes

Reaction equation

HRID 1588975 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[O:20][CH3:21])=[O:12]>C(O)C>[CH3:21][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[NH:13][C:11](=[O:12])[CH2:10][NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 416472-Chloro-N-(2-methoxyphenyl)acetamide

Product 1

HCID 14998796N-(2-Methoxyphenyl)-2-[(phenylmethyl)amino]acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To ethanol (100 mL) add benzylamine (35 g, 0.33 mol) and 2-chloro-N-(2-methoxyphenyl)acetamide (22 g, 0.11 mol). Stir and heat the reaction at 50° C. Monitor the progress of the reaction by thin-layer chromatography. Upon completion of the reaction remove the precipiate that has formed by suction filtration and discard. Evaporate the filtrate and partition the residue between ethyl acetate and 2N NaOH(aq). Separate the organic layer and dry it over Na2SO4. Remove the drying agent by filtration and remove the solvent in vacuo. Chromatograph the residue on silica gel (400 g) using hexane/EtOAc (3/1) as eluent to obtain the title compound.

Workup

  1. temperatureheat
  2. customthe reaction at 50° C
  3. customMonitor the progress of the reaction by thin-layer chromatography
  4. customUpon completion of the reaction remove the precipiate that
  5. customhas formed by suction filtration and discard
  6. customEvaporate the filtrate
  7. custompartition the residue between ethyl acetate and 2N NaOH(aq)
  8. customSeparate the organic layer
  9. dry with materialdry it over Na2SO4
  10. customRemove the drying agent
  11. filtrationby filtration
  12. customremove the solvent in vacuo

Sources & evidence

ORD record
ord-50518e9c9e464466bcbfbb1404c9a4af
Source dataset
uspto-grants-1993_06
Patent number
US05223623

Reaction notes

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