Phenol → 4-[1-Benzyl-3-(3-methoxy-phenyl)-piperidin-3-yl]-phenol

HRID 1633537

Reaktionsgleichung

Reaktionsgleichung von HRID 1633537
[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)(O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]1([OH:29])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Al+3].[Cl-].[Cl-].[Cl-]>[NH4+].[OH-]>[CH2:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([C:26]2[CH:27]=[CH:28][C:23]([OH:29])=[CH:24][CH:25]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 996PhenolHCID 6451240Aluminum(III) ChlorideHCID 136950931-Benzyl-3-(3-methoxyphenyl)piperidin-3-ol

Produkt 1

HCID 129687044-[1-Benzyl-3-(3-methoxy-phenyl)-piperidin-3-yl]-phenolAusbeute 59,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14923Ammonium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 1-benzyl-3-(3-methoxy-phenyl)-piperidin-3-ol (17.6 g, 73.1 mmol) in (CH2)2Cl2 (200 mL) was added phenol (16.7 g, 178 mmol) followed by portionwise addition (highly exothermic) of AlCl3 (23.3 g, 178 mmol). The reaction mixture was heated to reflux for 2 hours. The mixture was cooled to room temperature and was slowly poured into a mixture of crushed ice (50 mL) and 30% aq. NH4OH (120 mL). The mixture was stirred vigorously for 20 minutes and was then filtered through celite. The celite cake was washed with CH2Cl2 (200 mL). The organic layer was separated and the aqueous layer was washed with CH2Cl2 (3×100 mL). The combined organic layers were dried (MgSO4) and concentrated. The crude residue was purified by flash chromatography with hexanes/EtOAc (1:1) to afford 16.3 g of 4-[1-benzyl-3-(3-methoxy-phenyl)-piperidin-3-yl]-phenol 1HNMR (400 MHz, CDCl3) δ 7.39-7.21 (comp, 5 H), 7.19-7.05 (comp. 3H), 6.84 (s, 1H), 6.79 (d, 1H), 6.67-6.61 (comp, 3H), 3.73 (s, 3H), 3.50 (s, 2H), 2.86-2.79 (comp, 2H), 2.45-2.38 (comp, 2H), 2.21-2.19 (comp, 2H), 1.60-1.51 (comp, 2H); MS (M+1) 374.2.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationwas then filtered through celite
  4. washThe celite cake was washed with CH2Cl2 (200 mL)
  5. customThe organic layer was separated
  6. washthe aqueous layer was washed with CH2Cl2 (3×100 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated
  9. customThe crude residue was purified by flash chromatography with hexanes/EtOAc (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-86fef60b577e471f9d73f0c51cc31631
Quelldatensatz
uspto-grants-2003_01
Patentnummer
US06503905B1

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