Ether hydrochloride → 4-(2-Phenoxyethyl)piperidine

HRID 2095410Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2095410
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOCC>CO>[O:16]([CH2:15][CH2:14][CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

4

Edukt 2

HCID 10953452Ether hydrochlorideHCID 588081001-(Tert-butoxycarbonyl)-4-(2-phenoxyethyl)piperidine

Produkt 1

HCID 109547034-(2-Phenoxyethyl)piperidineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 1-(tert-butoxycarbonyl)-4-(2-phenoxyethyl)piperidine (220 mg, 0.72 mmol) in MeOH (2 mL) was added 2N anhydrous HCl/ether (0.5 mL, 1.0 mmol). The reaction mixture was stirred overnight. After evaporation, the residue was dissolved in deionized water. EtOAc was used to wash the aqueous layer before the pH was altered to approx. 9-10. The aqueous layer was extracted three times with CH2Cl2 and dried over Na2SO4. After evaporation, 4-(2-phenoxyethyl)piperidine (131.5 mg, 89%) was obtained as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 7.23 (m, 2H), 6.96 (m, 1H), 6.85 (m, 2H), 3.95 (m, 2H), 3.27 (m, 2H), 2.71 (m, 3H), 1.92 (m, 2H), 1.56 (m, 3H), 1.42 (m, 2H).

Aufarbeitung

  1. customAfter evaporation
  2. dissolutionthe residue was dissolved in deionized water
  3. washto wash the aqueous layer before the pH
  4. extractionThe aqueous layer was extracted three times with CH2Cl2
  5. dry with materialdried over Na2SO4
  6. customAfter evaporation

Quellen und Nachweise

ORD-Eintrag
ord-eabebc56f8c94ad491ea86d7c3a797c9
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08445684B2

Notizen zur Reaktion

Wird geladen…