Cyclohexene → 4-(Pyridin-3-yl)piperidin-4-ol

HRID 1490224

Reaktionsgleichung

Reaktionsgleichung von HRID 1490224
C([N:11]1[CH2:16][CH2:15][C:14]([C:18]2[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=2)([OH:17])[CH2:13][CH2:12]1)(OCC1C=CC=CC=1)=O.C1CCCCC=1>C(O)C.[Pd]>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([C:14]2([OH:17])[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]2)[CH:19]=1

Komponenten

5

Edukt 2

HCID 8079CyclohexeneHCID 21480587Benzyl 4-hydroxy-4-(pyridin-3-yl)piperidine-1-carboxylate

Produkt 1

HCID 49891674-(Pyridin-3-yl)piperidin-4-olAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 1-carbobenzyloxy-4-(3-pyridyl)piperidin-4-ol (described in example 87d) (3.17 g, 10.2 mmol) in ethanol (100 mL) was added 10% palladium on carbon (2.0 g). This was followed by cyclohexene (50 mL) in large excess. The reaction was heated to reflux under nitrogen for 2 h. The suspension was cooled, filtered and the catalyst rinsed with fresh ethanol. The filtrate was reduced in vacuo to yield 1.70 g (94%) of an off-white solid which did not require any additional purification. 1H NMR (D6 -DMSO, 300 MHz) 8.68 (d, J=2.0 Hz, 1H), 8.42 (dd, J=1.5, 4.6 Hz, 1H), 7.83 (ddd, J=1.9, 2.1, 4.0 Hz, 1H), 7.35 (dd, J=4.8, 8.0 Hz, 1H), 2.97 (ddd, J=2.3, 12.2 Hz, 2H), 2.78 (m, 2H), 1.86 (ddd, J=4.5, 12.9 Hz, 2H), 1.56 (m, 2H), 2.50 (m, 1H) MS (CI, CH4) m/z 179 (M+1,100), 207 (M+29,16), 161 (39)

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureto reflux under nitrogen for 2 h
  3. temperatureThe suspension was cooled
  4. filtrationfiltered
  5. washthe catalyst rinsed with fresh ethanol

Quellen und Nachweise

ORD-Eintrag
ord-8b62d2762c6f479794aadeae11917e69
Quelldatensatz
uspto-grants-1997_10
Patentnummer
US05681840

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