HCID 70045573, compound → HCID 70048187, compound

HRID 1419900Notes

Reaction equation

HRID 1419900 reaction equation
C([O:8][C:9]1[CH:32]=[CH:31][C:12]([C:13]([NH:15][CH2:16][CH2:17][N:18]2[CH2:23][CH2:22][C:21]([OH:30])([C:24]3C=CC=CC=3)[CH2:20][CH2:19]2)=[O:14])=[CH:11][CH:10]=1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[CH2:24]([C:21]1([OH:30])[CH2:20][CH2:19][N:18]([CH2:17][CH2:16][NH:15][C:13](=[O:14])[C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:32][CH:31]=2)[CH2:23][CH2:22]1)[C:9]1[CH:32]=[CH:31][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 70045573HCID 70045573, compound

Product 1

HCID 70048187HCID 70048187, compoundYield 201%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

Palladium on carbon (10%, 150 mg) was added to a solution of 4-benzyloxy-N-[2-(4-hydroxy-4-phenyl-piperidin-1-yl)-ethyl]-benzamide (500 mg, 1.12 mmol) in acetic acid (20 ml). The hydrogenation was complete after 3 h. The catalyst was removed by filtration through celite and the solvent was evaporated. Addition of sodium bicarbonate (10% aq. solution, 2 ml) and extraction with dichloromethane afforded N-[2-(4-benzyl-4-hydroxy-piperidin-1-yl)-ethyl]-4-hydroxy-benzamide (399 mg, 95%) as a light yellow solid.

Workup

  1. customThe catalyst was removed by filtration through celite
  2. customthe solvent was evaporated
  3. additionAddition of sodium bicarbonate (10% aq. solution, 2 ml) and extraction with dichloromethane

Sources & evidence

ORD record
ord-4e4ef8caf7d04191b5b3b676f91c2135
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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