Toluene → 4-Phenylpiperidine

HRID 2109628Notes

Reaction equation

HRID 2109628 reaction equation
Cl.C([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1)#N.[OH-].[K+].C1(C)C=CC=CC=1>O>[C:10]1([CH:4]2[CH2:5][CH2:6][NH:7][CH2:8][CH2:9]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 30849734-Phenylpiperidine-4-carbonitrile hydrochloride

Product 1

HCID 698734-Phenylpiperidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

4-Cyano-4-phenylpiperidine hydrochloride (10.0 g, 45.0 mmol) was combined with KOH pellets and stirred vigorously under Ar at 160° C. for 4 h. The reaction mix was cooled to RT and dissolved into toluene (100 ml) and H2O (100 ml). After separation of the layers, the aqueous layer was back-extracted two times with toluene. The combined organic layer was dried over Na2SO4, concentrated in vacuo, and dried under high vacuum, yielding a white solid.

Workup

  1. additionThe reaction mix
  2. temperaturewas cooled to RT
  3. customAfter separation of the layers
  4. extractionthe aqueous layer was back-extracted two times with toluene
  5. dry with materialThe combined organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customdried under high vacuum
  8. customyielding a white solid

Sources & evidence

ORD record
ord-16bf0908d86a48e3b1887b687d7f600a
Source dataset
uspto-grants-2009_04
Patent number
US07514564B2

Reaction notes

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