Sodium Hydroxide → 1-Benzyl-4-methyl-4-phenylpiperidine

HRID 382710Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 382710
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-].[OH-].[Na+]>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Produkt 1

HCID 108016621-Benzyl-4-methyl-4-phenylpiperidineAusbeute 104 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

1-Benzyl-4-methyl-piperidin-4-ol (4.81 g, 23.4 mmol, 1.00 equiv) was added to a suspension of AlCl3 (15.62 g, 117 mmol, 5.00 equiv) in benzene (100 mL) at room temperature under argon. The mixture was stirred at reflux for 24 hours, then cooled and poured cautiously into ice water (100 g of ice plus 50 mL of water). The aqueous phase was adjusted to pH 11-12 by addition of 6 N aqueous NaOH at 0° C., and extracted with EtOAc (3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, hexane-Et2O 19:1 to 9:1 followed by hexane-EtOAc 3:1) to give 3.23 g (52%) of brown oil, which was characterized, spectroscopically.

Aufarbeitung

  1. temperatureat reflux for 24 hours
  2. temperaturecooled
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic solutions were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, hexane-Et2O 19:1 to 9:1 followed by hexane-EtOAc 3:1)

Quellen und Nachweise

ORD-Eintrag
ord-cb7324df8aed4c1bab3962f4ef22d330
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310076B1

Notizen zur Reaktion

Wird geladen…