Dimethylformamide → HCID 18472220, compound

HRID 1387844Notes

Reaction equation

HRID 1387844 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:11]=[C:12]([CH:18]=[CH:19][CH:20]=2)[CH:13]=[CH:14][C:15]([OH:17])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:21](Cl)(=O)[C:22](Cl)=O.[CH3:27][N:28]([CH:30]=O)[CH3:29]>C1COCC1>[N:28]1([CH2:29][C:22]2[CH:21]=[CH:5][C:4]([NH:1][C:15](=[O:17])/[CH:14]=[CH:13]/[C:12]3[CH:18]=[CH:19][CH:20]=[C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)[CH:11]=3)=[CH:9][CH:8]=2)[CH2:30][CH2:10][CH2:6][CH2:7][CH2:27]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 53902412HCID 53902412, compound

Product 1

HCID 18472220HCID 18472220, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In THF (10 ml) was dissolved 3-(3-nitrophenyl)cinnamic acid (0.54 g), and to the solution were added oxalyl chloride (0.35 ml) and a drop of DMF. The mixture was stirred at room temperature for 1 hour and concentrated under reduced pressure. The residue was dissolved in THF (20 ml), and to the solution were added 1-(4-aminobenzyl)piperidine (0.38 g) and triethylamine (0.34 ml) at room temperature. The reaction mixture was stirred at room temperature for 2 hours, and to the mixture was added water (50 ml). The mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate to give (E)-N-[4-(piperidinomethyl)-phenyl]-3-(3-nitrophenyl)cinnamamide (Compound 75) (0.65 g) as pale yellow crystals.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in THF (20 ml)
  3. additionto the solution were added 1-(4-aminobenzyl)piperidine (0.38 g) and triethylamine (0.34 ml) at room temperature
  4. stirringThe reaction mixture was stirred at room temperature for 2 hours
  5. additionto the mixture was added water (50 ml)
  6. extractionThe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed with saturated sodium chloride solution
  8. dry with materialdried with anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-3ca92935581342b491215b5783e60110
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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