HCID 22335524, compound → HCID 9928893, compound

HRID 349397Notes

Reaction equation

HRID 349397 reaction equation
[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])/[C:18](/[CH3:26])=[CH:19]/[C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:12][CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1>CO.[Pd]>[N:1]1([CH:6]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:27])[CH:18]([CH3:26])[CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:12][CH:11]=2)[CH:7]([CH3:9])[CH3:8])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 1

HCID 22335524HCID 22335524, compound

Product 1

HCID 9928893HCID 9928893, compoundYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(±)-(E)-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]-2-methyl-3-phenyl-2-propenamide (0.0144 mol) in methanol (200 ml) was hydrogenated with palladium-on-charcoal 10% (0.52 g) as a catalyst at RT over a 5 hour period under a 1 bar pressure in a Parr apparatus. After uptake of hydrogen, the catalyst was filtered through celite and the solvent was evaporated. The residue was crystallized from 2-butanone/DIPE, yielding 4.9 g (94%) of (±)-N-[4-[1-(1H-imidazol-1-yl)-2-methylpropyl]phenyl]-α-methylbenzenepropanamide (compound 164).

Workup

  1. filtrationAfter uptake of hydrogen, the catalyst was filtered through celite
  2. customthe solvent was evaporated
  3. customThe residue was crystallized from 2-butanone/DIPE

Sources & evidence

ORD record
ord-0c1f784741584377b3c20845edf30792
Source dataset
uspto-grants-2007_02
Patent number
US07179825B2

Reaction notes

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