Phenylacetaldehyde → Benzeneethanamine, N-phenyl-

HRID 599505

反応式

HRID 599505 の反応式
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:22]1([CH2:28][CH:29]=O)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>CN(C=O)C.CO.CC(O)=O>[CH2:29]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 998PhenylacetaldehydeHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 74443Benzeneethanamine, N-phenyl-

試薬・触媒・溶媒 1

HCID 86614840DMF MeOH AcOH溶媒

実験手順

Sodium triacetoxyborohydride (5.46 g, 26 mmol) is added in small portions to a stirred solution of aniline (2.0 g, 21.5 mmol) and phenylacetaldehyde (2.83 g, 24 mmol) in dry DMF/MeOH/AcOH (87:10:3, 120 ml). After stirring at rt for 90 min, the volatiles are removed under reduced pressure. The residue is dissolved in dichloromethane (200 ml) and extracted twice with 1 N HCl. The combined aqueous layers are washed with EtOAc, then ammonium hydroxide solution is added to pH 9, and the mixture is extracted with dichloromethane. The solvent is evaporated, and the crude product is purified by silica gel chromatography (hexane/EtOAc, 5:1) affording pure title compound as a yellow oil.

後処理

  1. customthe volatiles are removed under reduced pressure
  2. dissolutionThe residue is dissolved in dichloromethane (200 ml)
  3. extractionextracted twice with 1 N HCl
  4. washThe combined aqueous layers are washed with EtOAc
  5. additionammonium hydroxide solution is added to pH 9
  6. extractionthe mixture is extracted with dichloromethane
  7. customThe solvent is evaporated
  8. customthe crude product is purified by silica gel chromatography (hexane/EtOAc, 5:1)

出典と根拠

ORDレコード
ord-55c5f3b2148745bf83448a41274cbb40
出典データセット
uspto-grants-2011_03
特許番号
US07897788B2

関連ノート

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