HCID 12988896, compound → Benzamide

HRID 2184945Notes

Reaction equation

HRID 2184945 reaction equation
C(N1CCCC(N([C:21]2[CH:22]=[C:23]([CH:31]=[CH:32][CH:33]=2)[C:24]([N:26](CC)CC)=[O:25])C2C=CC=CC=2)C1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[C:24]([NH2:26])(=[O:25])[C:23]1[CH:31]=[CH:32][CH:33]=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 12988896HCID 12988896, compound2×

Product 1

HCID 2331BenzamideYield 112.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 3-[N-(1-benzyl-piperidin-3-yl)-anilino]-N,N-diethyl benzamide (compound 17) (50 mg, 0.11 mmol) in EtOH (5 mL) was hydrogenated at 30 psi in the presence of a catalytic amount of Pd(OH)2 on carbon for 6 h. The mixture was filtered through Celite®, concentrated and the residue purified by chromatography (gradient, 9:1:0 to 9:1:0.5 EtOAc/heptane/Et3N) to yield the title compound 18 (15 mg, 36%) as a pale yellow viscous oil.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. concentrationconcentrated
  3. customthe residue purified by chromatography (gradient, 9:1:0 to 9:1:0.5 EtOAc/heptane/Et3N)

Sources & evidence

ORD record
ord-9af97d1a068847ba941bde703d8f488f
Source dataset
uspto-grants-2002_06
Patent number
US06399635B1

Reaction notes

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