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

HRID 2085398Notes

Reaction equation

HRID 2085398 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). To the resulting solution was added 10% palladium on carbon (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 magnesium sulfate and concentrated. The residual oil was purified by flash chromatography (CHCl3/MeOH/2 N NH3 in MeOH 100/4/0 to 100/20/10), giving 1-benzyl-4-methyl-4-phenylpiperidine (1.20 g) and 1.10 g (51%, 82% based on consumed starting material) of 4-methyl-4-phenylpiperidine: 1H NMRδ 1.24 (s, 3 H), 1.71 (m, 2 H), 2.06 (m, 2 H), 2.82 (m, 3 H), 2.94 (m, 2 H), 7.19 (m, 1 H), 7.32 (m, 4 H); 13C NMR δ 37.22, 38.54, 43.44, 47.74, 126.31, 127.43, 129.01, 149.73.

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 magnesium sulfate
  8. concentrationconcentrated
  9. customThe residual oil was purified by flash chromatography (CHCl3/MeOH/2 N NH3 in MeOH 100/4/0 to 100/20/10)

Sources & evidence

ORD record
ord-f59b8d7ad7c84b4db2f12d83f29f7241
Source dataset
uspto-grants-2004_04
Patent number
US06720324B2

Reaction notes

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