Acetic Acid → 4-(4-Methylphenyl)-3-phenylbutan-2-amine

HRID 1446419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1446419
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](=O)[CH3:11])=[CH:4][CH:3]=1.C(O)(=O)C.C([BH3-])#[N:24].[Na+]>N.CO>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]([NH2:24])[CH3:11])=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 126157934-(4-Methylphenyl)-3-phenylbutan-2-one

Produkt 1

HCID 222706534-(4-Methylphenyl)-3-phenylbutan-2-amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 222AmmoniaLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of the 4-(4-methylphenyl)-3-phenylbutan-2-one (308 mg, 1.29 mmol) in 7M ammonia in MeOH (5 mL) and acetic acid (3 mL) was added sodium cyanoborohydride (130 mg, 2.06 mmol) and the reaction stirred at room temperature overnight. The reaction was quenched by pouring into 2M sodium carbonate solution and extracted into EtOAc. The aqueous layer was salted and re-extracted. The combined organic extracts were dried over MgSO4 and concentrated to give the title compound as a mixture of 4 isomers which was used without further purification. LC-MS: m/e 240 (M+H)+ (2.22 min).

Aufarbeitung

  1. customThe reaction was quenched
  2. additionby pouring into 2M sodium carbonate solution
  3. extractionextracted into EtOAc
  4. extractionre-extracted
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a67520b81ce44da0875a707b2fd1fdb9
Quelldatensatz
uspto-grants-2010_02
Patentnummer
US07667053B2

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