HCID 53630737, compound → HCID 53630736, compound

HRID 655665Notes

Reaction equation

HRID 655665 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[C:6]([N:10]3[CH2:15][CH2:14][N:13]([CH2:16][CH2:17][CH2:18][O:19][C:20]4[CH:30]=[CH:29][C:23]([C:24]([NH:26][CH2:27][CH3:28])=[O:25])=[CH:22][C:21]=4[N+:31]([O-])=O)[CH2:12][CH2:11]3)=[CH:7][CH:8]=[CH:9][C:2]1=2>[C].[Pd].C(O)C>[NH2:31][C:21]1[CH:22]=[C:23]([CH:29]=[CH:30][C:20]=1[O:19][CH2:18][CH2:17][CH2:16][N:13]1[CH2:12][CH2:11][N:10]([C:6]2[C:3]3[CH:4]=[CH:5][S:1][C:2]=3[CH:9]=[CH:8][CH:7]=2)[CH2:15][CH2:14]1)[C:24]([NH:26][CH2:27][CH3:28])=[O:25]

Participants

4

Reactant 1

HCID 53630737HCID 53630737, compound

Product 1

HCID 53630736HCID 53630736, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

5% palladium carbon (0.8 g) was added to an ethanol solution (30 ml) of 4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-N-ethyl-3-nitrobenzamide (1.0 g, 2.1 mmol) and the mixture was subjected to catalytic reduction at room temperature under normal pressure. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Water was added to the residue and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and thereafter concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1→20:1). The purified product was concentrated under reduced pressure to obtain 3-amino-4-[3-(4-benzo[b]thiophen-4-yl-piperazin-1-yl)propoxy]-N-ethyl-benzamide (0.78 g, 83% yield) as yellow amorphous solid.

Workup

  1. customwas subjected to catalytic reduction at room temperature under normal pressure
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionWater was added to the residue
  5. extractionthe solution was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=30:1→20:1)
  9. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-03d875de5fe24007973f392987c28647
Source dataset
uspto-grants-2011_12
Patent number
US08071600B2

Reaction notes

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