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

HRID 466261Notes

Reaction equation

HRID 466261 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 78391,2-DibromoethaneCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-152b6223e7c541a2a2e589579881deff
Source dataset
uspto-grants-1992_10
Patent number
US05155212

Reaction notes

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