Ethyl Acetate → 1-{2-[4-(2-Benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-piperidine

HRID 445198Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 445198
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:22]1([CH2:28][CH2:29][O:30][C:31]2[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][CH:32]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=2)[C:10]=1[O:37][C:34]1[CH:33]=[CH:32][C:31]([O:30][CH2:29][CH2:28][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:36][CH:35]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 106090214-[2-(Piperidin-1-yl)ethoxy]phenolHCID 117029082-Benzyloxy-1-bromo-6-methoxy-naphthalene

Produkt 1

HCID 116774331-{2-[4-(2-Benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-piperidineAusbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
174 °C

Versuchsvorschrift

Combine toluene (200 mL), 2-benzyloxy-1-bromo-6-methoxy-naphthalene (30 g, 87.4 mmol), 4-(2-piperidin-1-yl-ethoxy)phenol (23.2 g, 105 mmol) and cesium carbonate (34.4 g, 105 mmol). Heat the mixture to reflux. Remove a portion of the toluene by distillation (100 mL). Add ethyl acetate (390 mg, 4.37 mmol) and copper triflate benzene complex (2.20 g, 4.37 mmol) to the reaction mixture and stir for 5 minutes. Remove the solvent by distillation and heat the resulting residue to 174° C. for 1.5 hours. Dissolve the residue in a mixture of ethyl acetate (200 mL) and aqueous HCl (1 N, 90 mL). Separate and concentrate the organic solution to a residue. Purify the residue by silica gel chromatography to give 1-{2-[4-(2-benzyloxy-6-methoxy-naphthalen-1-yloxy)-phenoxy]-ethyl}-piperidine (12.4 g, 26.2 mmol).

Aufarbeitung

  1. temperatureHeat the mixture
  2. temperatureto reflux
  3. customRemove a portion of the toluene
  4. distillationby distillation (100 mL)
  5. customRemove the solvent
  6. distillationby distillation
  7. dissolutionDissolve the residue
  8. additionin a mixture of ethyl acetate (200 mL) and aqueous HCl (1 N, 90 mL)
  9. customSeparate
  10. concentrationconcentrate the organic solution to a residue
  11. customPurify the residue by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-322eec60e91b4c408add059a6cdbde0e
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08476300B2

Notizen zur Reaktion

Wird geladen…