Benzene → 4-Phenylpiperidine

HRID 396605Notes

Reaction equation

HRID 396605 reaction equation
O[CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[Al+3].[Cl-].[Cl-].[Cl-].[CH:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+]>O>[C:12]1([CH:2]2[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 241BenzeneHCID 14798Sodium HydroxideHCID 79341Piperidin-4-olHCID 6451240Aluminum(III) Chloride

Product 1

HCID 698734-PhenylpiperidineYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Hydroxypiperidine (10.0 g, 98.9 mmol, 1.00 equiv) and AlCl3 (105.5 g, 791.2 mmol, 8.0 equiv) were stirred in refluxing benzene (350 mL) under a CaSO4 drying tube for 85 hours. The mixture was cooled to room temperature and poured carefully into ice (500 g) and water (50 mL) with stirring. With ice water cooling, the pH was adjusted to 10-11 by addition of solid NaOH. The resulting mixture was extracted with EtOAc (3×250 mL). The combined organic solutions were washed with brine, dried over MgSO4, and concentrated to give 6.5 g of 4-phenylpiperidine (yellow solid, 40%), which was characterized spectroscopically.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×250 mL)
  2. washThe combined organic solutions were washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f99334bf29a441918aca4e68186ab13c
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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