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

HRID 1355564

Reaktionsgleichung

Reaktionsgleichung von HRID 1355564
[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-]>>[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

4

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 %

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. NH4H (120 mL). The mixture was stirred vigorously for 20 mininutes 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, CDCl13) δ 7.39-7.21 (comp, 5H), 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-b6379f8f7e3b4f02b1cc3859b825bf48
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06586431B1

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