HCID 22600853, compound → HCID 22014421, compound

HRID 1870669Notes

Reaction equation

HRID 1870669 reaction equation
[CH2:1]([C:3]([N:19]([CH3:21])[CH3:20])([CH2:16][CH:17]=[CH2:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][OH:15])=[CH:8][CH:7]=1)=[O:5])[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]([N:19]([CH3:21])[CH3:20])([CH2:16][CH2:17][CH3:18])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][OH:15])=[CH:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 1

HCID 22600853HCID 22600853, compound

Product 1

HCID 22014421HCID 22014421, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

32.6 g (0.11 mol) of 2-ethyl-2-dimethylamino-1-(4-(2-hydroxyethoxy)phenyl)-pent-4-en-1-one according to Example A2 are dissolved in 220 ml of ethyl acetate, 1.6 g of palladium-on-carbon (5%) are added thereto and the mixture is then hydrogenated at 30° C. under normal pressure. After approximately 3 hours the absorption of hydrogen ceases (2.58 liters, 103% of the theoretical amount). The catalyst is removed by filtration and the solvent is distilled off using a rotary evaporator (RE). The oily residue is purified by flash-chromatography (petroleum ether/ethyl acetate 2:1). 27.4 g (84%) of a slightly yellowish oil remain.

Workup

  1. customis then hydrogenated at 30° C. under normal pressure
  2. customAfter approximately 3 hours the absorption of hydrogen ceases (2.58 liters, 103% of the theoretical amount)
  3. customThe catalyst is removed by filtration
  4. distillationthe solvent is distilled off
  5. customa rotary evaporator (RE)
  6. customThe oily residue is purified by flash-chromatography (petroleum ether/ethyl acetate 2:1)

Sources & evidence

ORD record
ord-7ad1c95e9d6d4bbd958d2a052109f4b0
Source dataset
uspto-grants-2000_08
Patent number
US06099122

Reaction notes

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