Aluminum(III) Chloride → 1-Benzyl-4-methyl-4-phenylpiperidine

HRID 1275206Notes

Reaction equation

HRID 1275206 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])(O)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Al+3].[Cl-].[Cl-].[Cl-]>C1C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:15])([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Product 1

HCID 108016621-Benzyl-4-methyl-4-phenylpiperidineYield 193.8%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 1-benzyl-4-methyl-4-piperidinol (3.6 g, 17.5 mmol) in 75 mL of benzene was added AlCl3 (11.7 g, 87.7 mmol) in one portion at room temperature. After stirring at room temperature for 30 min, the reaction mixture was heated to reflux for 8 h. The red colored solution was allowed to cool and then poured over 100 g of ice-water. It was extracted with EtOAc (2×100 mL) and the organic layer was washed with solution of Rochelle's salt. The organic layer was separated, dried over Na2SO4, filtered and the solvent was removed in vacuo to obtain 1-benzyl-4-methyl-4-phenyl piperidine as a red oil (4.5 g, 97% yield). It was used in the next step without further purification.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 8 h
  3. temperatureto cool
  4. extractionIt was extracted with EtOAc (2×100 mL)
  5. washthe organic layer was washed with solution of Rochelle's salt
  6. customThe organic layer was separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-8bf61090572c4c30bb91387f287f5590
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

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