Sodium Hydroxide → 1-Benzyl-4-methyl-4-phenylpiperidine

HRID 964256Notes

Reaction equation

HRID 964256 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-].[OH-].[Na+]>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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 6451240Aluminum(III) ChlorideHCID 108459131-Benzyl-4-methylpiperidin-4-ol

Product 1

HCID 108016621-Benzyl-4-methyl-4-phenylpiperidineYield 104%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

1-Benzyl-4-methyl-piperidin-4-ol (4.81 g, 23.4 mmol, 1.00 equiv) was added to a suspension of AlCl3 (15.62 g, 117 mmol, 5.00 equiv) in benzene (100 ml) at room temperature under argon. The mixture was stirred at reflux for 24 hours, then cooled and poured cautiously into ice water (100 g of ice plus 50 ml of water). The aqueous phase was adjusted to pH 11-12 by addition of 6N aqueous NaOH at 0° C., and extracted with EtOAc (3×100 mL). The combined organic solutions were dried over MgSO4 and concentrated. The residue was purified by flash chromatography (SiO2, hexane-Et2O 19:1 to 9:1 followed by hexane-EtOAc 3:1) to give 3.23 g (52%) of brown oil, which was characterized spectroscopically.

Workup

  1. temperatureat reflux for 24 hours
  2. temperaturecooled
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic solutions were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (SiO2, hexane-Et2O 19:1 to 9:1 followed by hexane-EtOAc 3:1)

Sources & evidence

ORD record
ord-3917f045ff4f4af38ee1f52513450e03
Source dataset
uspto-grants-1998_06
Patent number
US05767131

Reaction notes

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