Ethanol → (E)-3-Benzylidene-1-(triphenylmethyl)piperidin-4-ol

HRID 1171634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1171634
[CH:1](=[C:8]1/[CH2:9][N:10]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][CH2:12][C:13]/1=[O:14])/[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[BH4-].[Na+].[Cl-].[NH4+]>ClCCl>[CH:1](=[C:8]1/[CH2:9][N:10]([C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:11][CH2:12][CH:13]/1[OH:14])/[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 68765712(E)-3-Benzylidene-1-(triphenylmethyl)piperidin-4-one

Produkt 1

HCID 68764908(E)-3-Benzylidene-1-(triphenylmethyl)piperidin-4-olAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (E)-3-benzylidene-1-(triphenylmethyl)piperidin-4-one (3.91 g) in a mixed solvent of ethanol (30 ml) and dichloromethane (30 ml) was added sodium borohydride (0.34 g) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hours. After stirring, saturated aqueous ammonium chloride solution was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and hexane (3:7) as the eluent to afford the title compound (2.61 g, yield: 66%) as a colourless amorphous solid.

Aufarbeitung

  1. temperaturecooling
  2. stirringAfter stirring
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by chromatography on a silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-aaabdc0934d84cf69f0ef928171fa98b
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07829580B2

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