Hydrochloric Acid → 4-[2-(4-Methylphenylsulfanyl)phenyl]-3,6-dihydro-2H-pyridine

HRID 722116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 722116
Cl.C(OC([N:9]1[CH2:14][CH2:13][C:12]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22][C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(O)[CH2:11][CH2:10]1)=O)(C)(C)C.[OH-].[Na+]>C(O)(=O)C>[CH3:29][C:26]1[CH:27]=[CH:28][C:23]([S:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:12]2[CH2:13][CH2:14][NH:9][CH2:10][CH:11]=2)=[CH:24][CH:25]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 218649151-Tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol

Produkt 1

HCID 98143014-[2-(4-Methylphenylsulfanyl)phenyl]-3,6-dihydro-2H-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Concentrated aq hydrochloric acid (10 ml) was added to a stirred solution of 1-tert-butoxycarbonyl-4-[2-(4-methylphenylsulfanyl)phenyl]piperidin-4-ol (0.84 g, 2.1 mmol) in acetic acid (30 mL). The solution was boiled under reflux overnight, cooled to room temperature and then stirred in an ice bath. An aqueous solution of NaOH (9.1 M, 40 mL) was slowly added and the unclear solution was extracted with ethyl acetate (2×40 ml). The combined organic phases were dried (MgSO4) and the solvents evaporated in vacuo. The crude material (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50° C. and a solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was slowly added. The target compound was collected as a white oxalic salt. 1H (DMSO-d6) δ 7.3–7.2 (m, 7H); 7.15 (m, 1H); 7.00 (m, 1H); 5.6 (d, 1H); 3.7 (d, 2H); 3.25 (t, 2H); 2.6 (m, 2H); 2.3 (s, 3H). LC/MS (m/z) 282.2 (MH+); RT=2.24; purity (UV, ELSD): 99%, 100%; yield: 0.31 g (40%).

Aufarbeitung

  1. temperatureunder reflux overnight
  2. extractionthe unclear solution was extracted with ethyl acetate (2×40 ml)
  3. dry with materialThe combined organic phases were dried (MgSO4)
  4. customthe solvents evaporated in vacuo
  5. dissolutionThe crude material (0.48 g) was dissolved in ethyl acetate (3.2 mL) at 50° C.
  6. additiona solution of oxalic acid (0.11 g) in EtOH (3.2 mL) was slowly added
  7. customThe target compound was collected as a white oxalic salt
  8. customRT=2.24

Quellen und Nachweise

ORD-Eintrag
ord-69d120da63ed4b4f8e8a16ccb440fd8f
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07138407B2

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