Phenylacetaldehyde → 2-Phenyl-N-(2-phenylethyl)ethan-1-amine

HRID 599508

Reaktionsgleichung

Reaktionsgleichung von HRID 599508
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:15]([NH2:23])[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[C:24]1([CH2:30][CH:31]=O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.OP([O-])(O)=O.[K+]>CO>[CH2:15]([NH:23][CH2:31][CH2:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 998PhenylacetaldehydeHCID 1001PhenethylamineHCID 516951Monobasic potassium phosphateHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 227912-Phenyl-N-(2-phenylethyl)ethan-1-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Sodiumtriacetoxyborohydride (8.87 g, 41.3 mmol) is added in small portions at 0° C. to a stirred solution of phenethylamine (5.0 g, 41.3 mmol) and phenylacetaldehyde (4.96 g, 41.3 mmol) in methanol (50 ml). The reaction mixture is stirred at rt overnight, poured onto saturated aqueous KH2PO4 solution and extracted twice with EtOAc. The solvent is evaporated, the residue is taken up in 1N HCl and washed twice with dichloromethane. The aqueous layer is adjusted to pH 9 by the addition of ammonium hydroxide solution and extracted with dichloromethane. Drying the combined organic layers over Na2SO4 and evaporating the solvents give crude title compound as a pale yellow oil.

Aufarbeitung

  1. extractionextracted twice with EtOAc
  2. customThe solvent is evaporated
  3. washwashed twice with dichloromethane
  4. additionThe aqueous layer is adjusted to pH 9 by the addition of ammonium hydroxide solution
  5. extractionextracted with dichloromethane
  6. dry with materialDrying the combined organic layers over Na2SO4
  7. customevaporating the solvents

Quellen und Nachweise

ORD-Eintrag
ord-e6c65e702b144d18988ae03d0198767e
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897788B2

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