Phenylacetaldehyde → Benzeneethanamine, N-phenyl-

HRID 599505

Reaction equation

HRID 599505 reaction equation
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

Participants

5

Reactant 3

HCID 998PhenylacetaldehydeHCID 6115AnilineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 74443Benzeneethanamine, N-phenyl-

Reagents, catalysts & solvents 1

HCID 86614840DMF MeOH AcOHSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-55c5f3b2148745bf83448a41274cbb40
Source dataset
uspto-grants-2011_03
Patent number
US07897788B2

Linked notes

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