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2-Chlorophenol → 1-Benzyl-4-(4-methoxybenzylidene)-piperidine

HRID 895463
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 895463
C(OC(N1CC[CH:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2Cl)CC1)=O)(C)(C)C.C(O[C:27]([N:29]1[CH2:34][CH2:33][CH:32](O)[CH2:31][CH2:30]1)=O)(C)(C)C.Cl[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1O.[C:44]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>CCOC(C)=O>[CH2:27]([N:29]1[CH2:30][CH2:31][C:32](=[CH:44][C:18]2[CH:17]=[CH:16][C:15]([O:14][CH3:11])=[CH:20][CH:19]=2)[CH2:33][CH2:34]1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 72452-ChlorophenolHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 16732586Tert-butyl 4-(2-chlorophenoxy)piperidine-1-carboxylate

Produkt 1

HCID 22378870
1-Benzyl-4-(4-methoxybenzylidene)-piperidine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(2-Chlorophenoxy)-piperidine-1-carboxylic acid tert-butyl ester (10.6) This compound was prepared from 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (9) (3.505 g; 17.4 mmol), 2-chloro-phenol (3.375 g; 26.3 mmol), triphenylphosphine (6.002 g; 22.9 mmol) and DIAD (4.30 mL; 21.8 mmol) in a manner analogous to 10.5. After 8 days, EtOAc (200 mL) was added to the crude reaction mixture and the solution washed with 50% saturated NaHCO3 (50 mL), saturated NaHCO3 (2×25 mL) and saturated NaCl (2×25 mL) then dried (MgSO4), filtered and concentrated to a viscous liquid. Ether (50 mL) and hexanes (50 mL) were added and this was allowed to stand overnight; whereupon the precipitate was removed by filtration and the filtrate partially concentrated. More material precipitated, which was also removed by filtration, and the filtrate was concentrated to an oil. The product was partially purified on basic alumina (160 mL), eluting with 8:1 hexanes:EtOAc, giving a clear, colorless viscous liquid (5.12 g; 94% crude yield). LC (method A) tR=11.50 min; ESIMS 312.1/314.1 (1/0.3) [MH+], 296.9/298.9 (100/34) [MH+−C4H9+CH3CN], 255.9/257.8 (41/12) [MH+−C4H9], 212.0/214.0 (4/1) [MH+−C4H9−CO2]

Aufarbeitung

  1. customreaction mixture
  2. washthe solution washed with 50% saturated NaHCO3 (50 mL), saturated NaHCO3 (2×25 mL) and saturated NaCl (2×25 mL)
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a viscous liquid
  6. additionEther (50 mL) and hexanes (50 mL) were added
  7. waitto stand overnight
  8. customwhereupon the precipitate was removed by filtration
  9. concentrationthe filtrate partially concentrated
  10. customMore material precipitated
  11. customwhich was also removed by filtration
  12. concentrationthe filtrate was concentrated to an oil
  13. customThe product was partially purified on basic alumina (160 mL)
  14. washeluting with 8:1 hexanes
  15. customEtOAc, giving a clear, colorless viscous liquid (5.12 g; 94% crude yield)

Quellen und Nachweise

ORD-Eintrag
ord-31bfcc6e231d426eb370313a1463bff3
Quelldatensatz
uspto-grants-2005_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06916804B2

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