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

HRID 1371883Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1371883
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-588f425d1301444ebba0a665277b2045
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07157488B2

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