2-[(4-Nitro-phenyl)methyl]-1-(4-fluorophenyl)-2-dimethylamino-1-butanone → 2-[(4-Aminophenyl)methyl]-1-(4-fluorophenyl)-2-dimethylamino-1-butanone

HRID 15246Notes

Reaction equation

HRID 15246 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:23]([CH3:25])[CH3:24])([CH2:21][CH3:22])[C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([N:23]([CH3:25])[CH3:24])([CH2:21][CH3:22])[C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 686377532-[(4-Nitro-phenyl)methyl]-1-(4-fluorophenyl)-2-dimethylamino-1-butanoneHCID 178418361HCID 178418361, compound2×

Product 1

HCID 686385232-[(4-Aminophenyl)methyl]-1-(4-fluorophenyl)-2-dimethylamino-1-butanone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

7.0 g Palladium on charcoal (5%) are added to solution of 69.5 g (0.178 mol) 2-[(4-nitro-phenyl)methyl]-1-(4-fluorophenyl)-2-dimethylamino-1-butanone in 700 ml ethanol in an hydrogenation autoclave. Hydrogen is entered with a continuous increase of pressure to 5 bar at temperature between room temperature and 40° C. After 25 hours no further hydrogen uptake is observed. The catalyst is filtered off and the crude product obtained as yellowish oil after evaporation of the solvent. Thin film chromatography shows a main product and some minor by-products. The crude material is used without further purification in the next reaction step.

Workup

  1. temperaturea continuous increase of pressure to 5 bar at temperature between room temperature and 40° C
  2. filtrationThe catalyst is filtered off

Sources & evidence

ORD record
ord-c0a59aec5c9b49048cc6d6e49041b7d0
Source dataset
uspto-grants-2010_06
Patent number
US07732504B2

Reaction notes

Loading…