HCID 54382316, compound → HCID 18357333, compound

HRID 428314Notes

Reaction equation

HRID 428314 reaction equation
[CH:1]([N:4]([CH:25]([CH3:27])[CH3:26])[C:5](=[O:24])[CH:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:3])[CH3:2]>C(O)C.[Pd]>[CH:25]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5](=[O:24])[CH2:6][CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:22])([F:23])[F:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:27])[CH3:26]

Participants

4

Reactant 1

HCID 54382316HCID 54382316, compound

Product 1

HCID 18357333HCID 18357333, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N,N-diisopropyl-3-(2-trifluoromethylphenyl)-3-phenylpropenamide (2.95 g, 8.1 mmol) in ethanol (50 mL) was hydrogenated over Pd/C (10%, 300 mg) at normal pressure for 24 h. The catalyst was filtered off, the solvent partly evaporated and the product collected after crystallisation. Yield 1.78 g (60%). 1H NMR (CDCl3-d) δ1.16 (m, 6H), 1.30 (m, 6H), 2.86 (dd, 1H), 3.11 (dd, 1H), 3.41 (m, 1H), 4.03 (m, 1H), 5.12 (m,1H) and 7.10-7.78 (m, 9H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent partly evaporated
  3. customthe product collected
  4. customafter crystallisation

Sources & evidence

ORD record
ord-41aa1f36eba1409794c95fce62e58c3e
Source dataset
uspto-grants-2001_11
Patent number
US06313132B1

Reaction notes

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