Iodine → 1-(1-Phenylcyclohexyl)-4-hydroxypiperidine

HRID 1588221Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1588221
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg].II.C([C:13]1([N:19]2[CH2:24][CH2:23][CH:22]([OH:25])[CH2:21][CH2:20]2)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)#N>O1CCCC1.BrCCBr>[C:2]1([C:13]2([N:19]3[CH2:20][CH2:21][CH:22]([OH:25])[CH2:23][CH2:24]3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 807IodineHCID 7961BromobenzeneHCID 5462224MagnesiumHCID 100589041-(4-Hydroxypiperidin-1-yl)cyclohexane-1-carbonitrile

Produkt 1

HCID 988401-(1-Phenylcyclohexyl)-4-hydroxypiperidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 78391,2-DibromoethaneKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To bromobenzene (4.1 ml) and magnesium turnings (4 g) in 200 ml dry tetrahydrofuran under nitrogen was added a crystal of iodine and 10 drops of 1,2-dibromoethane. After small bubbles began to form, the reaction was stirred and heated to reflux for 4 hours. After cooling to room temperature 1-(1-cyanocyclohexyl)-4-hydroxypiperidine (2 g) was added. After 17 hours, the reaction was filtered, 120 ml saturated ammonium chloride was added and the mixture was extracted with ethyl ether. The ether layer was dried and the solvent was removed in vacuo. The residue was chromatographed on silica gel eluted with the appropriate mixture of methanol and chloroform to yield pure 1-(1-phenylcyclohexyl)-4-hydroxypiperidine.

Aufarbeitung

  1. customto form
  2. temperatureheated
  3. temperatureto reflux for 4 hours
  4. additionwas added
  5. filtrationthe reaction was filtered
  6. addition120 ml saturated ammonium chloride was added
  7. extractionthe mixture was extracted with ethyl ether
  8. dry with materialThe ether layer was dried
  9. customthe solvent was removed in vacuo
  10. customThe residue was chromatographed on silica gel
  11. washeluted with the appropriate mixture of methanol and chloroform

Quellen und Nachweise

ORD-Eintrag
ord-ca2a8b9fd6614c1eb17e7bc654ca665a
Quelldatensatz
uspto-grants-1993_06
Patentnummer
US05221629

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