Acetic Acid → (4-Amino-3,5-difluoro-phenyl)-(4-ethyl-piperazin-1-yl)-methanone

HRID 912167Notes

Reaction equation

HRID 912167 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH3:28])[CH2:23][CH2:22]2)=[O:20])[CH:5]=[C:6]([F:18])[C:7]=1[NH:8]CC1C=CC(OC)=CC=1.C(O)(=O)C>CO.[Pd]>[NH2:8][C:7]1[C:6]([F:18])=[CH:5][C:4]([C:19]([N:21]2[CH2:22][CH2:23][N:24]([CH2:27][CH3:28])[CH2:25][CH2:26]2)=[O:20])=[CH:3][C:2]=1[F:1]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 59244390[3,5-Difluoro-4-(4-methoxy-benzylamino)-phenyl]-(4-ethyl-piperazin-1-yl)-methanone

Product 1

HCID 55160008(4-Amino-3,5-difluoro-phenyl)-(4-ethyl-piperazin-1-yl)-methanoneYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

To a solution of [3,5-difluoro-4-(4-methoxy-benzylamino)-phenyl]-(4-ethyl-piperazin-1-yl)-methanone (11.8 g, 30.4 mmol) obtained in Step C in methanol (150 ml), palladium black was added, followed by stirring for 24 hours under a hydrogen gas atmosphere. Acetic acid (15 ml) was added, followed by further stirring for 17 hours at room temperature. This was filtered through Celite, and the solvent was distilled off under reduced pressure. This was purified by silica gel column chromatography (dichloromethane/methanol=100/1 to 10/1), to obtain the desired compound as a brown solid (7.42 g, 91%).

Workup

  1. stirringby further stirring for 17 hours at room temperature
  2. filtrationThis was filtered through Celite
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThis was purified by silica gel column chromatography (dichloromethane/methanol=100/1 to 10/1)

Sources & evidence

ORD record
ord-cb6bcb2fc5534672a438269b29a46d33
Source dataset
uspto-grants-2011_09
Patent number
US08022205B2

Reaction notes

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