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

HRID 1371883ノート

反応式

HRID 1371883 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-588f425d1301444ebba0a665277b2045
出典データセット
uspto-grants-2007_01
特許番号
US07157488B2

反応ノート

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