1-Bromonaphthalene → 1-Benzyl-4-hydroxy-4-(naphth-1-yl)piperidine

HRID 380542Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 380542
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C([Li])(CC)C.[CH2:17]([N:24]1[CH2:29][CH2:28][C:27](=[O:30])[CH2:26][CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCCC1>[CH2:17]([N:24]1[CH2:29][CH2:28][C:27]([OH:30])([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][CH:3]=2)[CH2:26][CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

5

Edukt 3

HCID 70011-BromonaphthaleneHCID 192201-Benzyl-4-piperidoneHCID 178418400CID 53628100

Produkt 1

HCID 183653421-Benzyl-4-hydroxy-4-(naphth-1-yl)piperidineAusbeute 32,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A solution of 10.0 gm (42.2 mMol) 1-bromonaphthalene in 180 mL tetrahydrofuran was cooled to −78° C. and then to this solution were added 48.7 mL (63.3 mMol) sec-butyllithium (1.3 M in cyclohexane). After stirring for about 1.5 hours, a solution of 8.2 mL (44.3 mMol) 1-benzylpiperidin-4-one in 60 mL tetrahydrofuran was added dropwise and the resulting mixture was allowed to warm gradually to room temperature. The reaction was then quenched by the addition of 2 N sodium hydroxide. The resulting mixture was extracted with diethyl ether. The organic extracts were combined, washed with saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with dichloromethane containing from 0 to 2% methanol. Fractions containing product were combined and concentrated under reduced pressure to provide 4.34 gm (32%) of the desired compound as a white foam.

Aufarbeitung

  1. customThe reaction was then quenched by the addition of 2 N sodium hydroxide
  2. extractionThe resulting mixture was extracted with diethyl ether
  3. washwashed with saturated aqueous sodium chloride
  4. concentrationconcentrated under reduced pressure
  5. washeluting with dichloromethane containing from 0 to 2% methanol
  6. additionFractions containing product
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-4762a0d37cba43668d7016e4f3bdedf6
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06303627B1

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