HCID 18469985, compound → HCID 10038090, compound

HRID 2228452Notes

Reaction equation

HRID 2228452 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:21])[CH2:9][CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)=[CH:4][CH:3]=1.[H][H]>[Pd].C(OCC)(=O)C.O1CCCC1>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH2:10][CH2:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[O:21])=[CH:13][CH:14]=1

Participants

6

Reactant 2

HCID 18469985HCID 18469985, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10038090HCID 10038090, compoundYield 78%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-4-(4-nitrophenyl)butan-1-one (0.5 g, 1.7 mmol) and 10% palladium on carbon (0.06 g) in ethyl acetate (15 mL) and tetrahydrofuran (5 mL) was hydrogenated at room temperature using the hydrogen balloon. The catalyst was removed by filtration, and the filtrate concentrated in vacuo. Purification by silica gel chromatography, eluting with 10% ethyl acetate/hexane gave the title compound as a white solid (0.34 g, 78%). The product was used in the next step.

Workup

  1. customwas hydrogenated at room temperature
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customPurification by silica gel chromatography
  5. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-c664cdbb863641db9ba46c4c19d1d849
Source dataset
uspto-grants-2002_07
Patent number
US06417186B1

Reaction notes

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