Water → 1-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine

HRID 1197880

Reaktionsgleichung

Reaktionsgleichung von HRID 1197880
C([Li])CCC.Br[C:7]1[C:16]2[O:15][CH2:14][CH2:13][O:12][C:11]=2[CH:10]=[CH:9][CH:8]=1.[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.O>CCCCCC.O1CCCC1>[CH2:17]([N:24]1[CH2:29][CH2:28][C:27]([OH:30])([C:7]2[C:16]3[O:15][CH2:14][CH2:13][O:12][C:11]=3[CH:10]=[CH:9][CH:8]=2)[CH2:26][CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 192201-Benzyl-4-piperidoneHCID 187872685-Bromo-2,3-dihydro-1,4-benzodioxineHCID 178418339Butyllithium

Produkt 1

HCID 190820021-Benzyl-4-hydroxy-4-(1,4-benzodioxan-5-yl)piperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
-60 °C

Versuchsvorschrift

23.3 ml of a 1.6M solution of butyllithium in hexane are added dropwise to a solution, previously cooled to -60° C., of 8 g of 5-bromo-1,4-benzodioxane in 400 ml of tetrahydrofuran. When the addition is complete, the mixture is stirred at -60° C. for 5 minutes and a solution of 8 g of 1-benzylpiperid-4-one in 100 ml of tetrahydrofuran is then added dropwise. The mixture is stirred for 2 hours at -40° C. and then for 2 hours at ambient temperature before hydrolyzing using 80 ml of water.

Aufarbeitung

  1. additionWhen the addition
  2. stirringThe mixture is stirred for 2 hours at -40° C.
  3. waitfor 2 hours at ambient temperature before hydrolyzing using

Quellen und Nachweise

ORD-Eintrag
ord-366b5ed7becd4b6a9584111eca65bb6a
Quelldatensatz
uspto-grants-1994_01
Patentnummer
US05278185

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