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

HRID 728919Notes

Reaction equation

HRID 728919 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 precipitate 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 precipitate 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-1df82836c36e42c6a115b68dbe6395f8
Source dataset
uspto-grants-1991_09
Patent number
US05051422

Reaction notes

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