Acetic Acid → N-(2-(3-Chlorophenyl)ethyl)-3-benzoylbenzylamine

HRID 1371883Notes

Reaction equation

HRID 1371883 reaction equation
[C:1]([C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:17][C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][NH2:26])[CH:21]=[CH:22][CH:23]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO.ClC(Cl)C.CCOC(C)=O>[Cl:17][C:18]1[CH:19]=[C:20]([CH2:24][CH2:25][NH:26][CH2:12][C:11]2[CH:14]=[CH:15][CH:16]=[C:9]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:10]=2)[CH:21]=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 1393813-ChlorophenethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 130201683-Benzoylbenzaldehyde

Product 1

HCID 21071618N-(2-(3-Chlorophenyl)ethyl)-3-benzoylbenzylamine

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine 3-benzoylbenzaldehyde (0.45 g, 2.1 mmol), and (3-chlorophenyl)ethylamine (0.3 ml, 2.1 mmol) and 3 Å molecular sieves (1.0 g) in MeOH (30 ml). Heat to reflux. After 3 hours, cool, filter, and concentrate to give a residue. Dissolve the residue in dichloroethane (20 ml), add acetic acid (0.12 ml, 2.1 mmol) and sodium triacetoxyborohydride (0.6 g, 2.94 mmol) and stir at ambient temperature. After 2 hours, concentrate the reaction mixture and add dichloromethane (90 ml) and extract sequentially with distilled water (50 ml) and then brine (50 ml). Dry the organic layer over Na2SO4 and give a residue. Chromatograph the residue on silica gel eluting with EtOAc to give the title compound as the base.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. filtrationfilter
  4. concentrationconcentrate
  5. customto give a residue
  6. waitAfter 2 hours
  7. concentrationconcentrate the reaction mixture
  8. additionadd dichloromethane (90 ml)
  9. extractionextract sequentially with distilled water (50 ml)
  10. dry with materialDry the organic layer over Na2SO4
  11. customgive a residue

Sources & evidence

ORD record
ord-588f425d1301444ebba0a665277b2045
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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