HCID 22729892, compound → HCID 9819904, compound

HRID 2085457Notes

Reaction equation

HRID 2085457 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11]([C:21]2[CH:33]=[CH:32][C:24]([C:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[O:26])=[CH:23][CH:22]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[CH2:30]([N:27]([CH2:28][CH3:29])[C:25](=[O:26])[C:24]1[CH:23]=[CH:22][C:21]([C:11]2([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([OH:20])[CH:15]=3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[CH:33][CH:32]=1)[CH3:31]

Participants

4

Reactant 1

HCID 22729892HCID 22729892, compound

Product 1

HCID 9819904HCID 9819904, compoundYield 84.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 4-[1-Benzyl-4-(3-hydroxy-phenyl)-piperidin-4-yl]-N,N-diethylbenzamide (1.11 g, 2.49 mmol) in acetic acid (8 mL) in a Parr pressure bottle was added Pd(OH)2 (10% on carbon, 0.4 g). The reaction mixture was shaken under 50 psi of H2 for 20 hours. The reaction mixture was then filterd through celite. The celite cake was washed with EtOAc (250 mL) and the organic layer was concentrated to remove the acetic acid. The residue was partitioned between CH2Cl2 (10 mL) and 30% aqueous NH40H (10 mL). The organic layer was separated and the aqueous layer was washed with CH2Cl2 (3×20 mL). The combined organic layers were dried (MgSO4) and concentrated to afford 0.74 g of N,N-Diethyl-4-[4-(3-hydroxy-phenyl)-piperidin-4-yl]-benzamide (83% yield) which was used with no further purification. 1HNMR (400 MHz, CD3CO2D) δ 7.24-7.06 (comp, 5H), 6.75 (s, 1H), 6.70 (d, 1H), 6.58 (d, 1H), 3.49-3.40 (comp, 2H), 3.21-3.15 (comp, 2H), 2.90-2.85 (comp, 4H), 2.39-2.33 (comp, 4H), 1.20-1.15 (comp, 3H), 1.08-1.02 (comp, 3H); MS (M+1) 353.2.

Workup

  1. washThe celite cake was washed with EtOAc (250 mL)
  2. concentrationthe organic layer was concentrated
  3. customto remove the acetic acid
  4. customThe residue was partitioned between CH2Cl2 (10 mL) and 30% aqueous NH40H (10 mL)
  5. customThe organic layer was separated
  6. washthe aqueous layer was washed with CH2Cl2 (3×20 mL)
  7. dry with materialThe combined organic layers were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8046e642bfb44adc978078985cb7dc3a
Source dataset
uspto-grants-2004_04
Patent number
US06720336B2

Reaction notes

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