1-Benzyl-4-methyl-4-phenylpiperidine → 4-Methyl-4-phenylpiperidine

HRID 396653Notes

Reaction equation

HRID 396653 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)=O>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([CH3:20])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH3:20][C:11]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 1

HCID 108016621-Benzyl-4-methyl-4-phenylpiperidine

Product 2

HCID 30195114-Methyl-4-phenylpiperidineHCID 108016621-Benzyl-4-methyl-4-phenylpiperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 284Formic AcidSolvent

Procedure

Freshly prepared methanolic formic acid solution (4.4% by weight, 70 mL) was added to 1-benzyl-4-methyl-4-phenylpiperidine (3.23 g, 12.2 mmol, 1.00 equiv). To the resulting solution was added palladium on carbon (10% Pd, 2.00 g). The mixture was stirred at room temperature for 24 hours. The solid was filtered out and washed with MeOH (30 mL), H2O (15 mL), CH2Cl2 (30 mL) and MeOH (15 mL). The combined filtrate and washings were concentrated, and the residue was dissolved in CH2Cl2 (50 mL) and H2O (10 mL). The aqueous phase was adjusted to pH 11 by addition of 1 N aqueous NaOH. The organic phase was separated, dried over MgSO4 and concentrated. The residual oil was purified by flash chromatography (SiO2, CHCl3-MeOH-NH3 (2.0 M in MeOH) 100:4:0 to 100:20:10) to afford 1.20 g of 1-benzyl-4-methyl-4-phenylpiperidine and 1.10 g (51%, 82% based on unrecovered starting material) of 4-methyl-4-phenylpiperidine, which was characterized spectroscopically.

Workup

  1. filtrationThe solid was filtered out
  2. washwashed with MeOH (30 mL), H2O (15 mL), CH2Cl2 (30 mL) and MeOH (15 mL)
  3. concentrationThe combined filtrate and washings were concentrated
  4. dissolutionthe residue was dissolved in CH2Cl2 (50 mL)
  5. additionThe aqueous phase was adjusted to pH 11 by addition of 1 N aqueous NaOH
  6. customThe organic phase was separated
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe residual oil was purified by flash chromatography (SiO2, CHCl3-MeOH-NH3 (2.0 M in MeOH) 100:4:0 to 100:20:10)

Sources & evidence

ORD record
ord-73cabdac9f18422a8b375927fd812d61
Source dataset
uspto-grants-2003_08
Patent number
US06608086B2

Reaction notes

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