Water → (E)-N-[4-[1-(3,4-methylenedioxybenzyl)-4-piperazinylmethyl]phenyl]-3-(4-methylphenyl)cinnamamide

HRID 1277076Notes

Reaction equation

HRID 1277076 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[CH:14]=2)=[CH:5][CH:4]=1.[CH2:27]1[O:42][C:41]2[CH:40]=[CH:39][C:31]([CH2:32][N:33]3[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]3)=[CH:30][C:29]=2[O:28]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH2:27]1[O:42][C:41]2[CH:40]=[CH:39][C:31]([CH2:32][N:33]3[CH2:38][CH2:37][N:36]([CH2:2][C:3]4[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]5[CH:18]=[CH:17][CH:16]=[C:15]([C:19]6[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=6)[CH:14]=5)=[CH:5][CH:4]=4)[CH2:35][CH2:34]3)=[CH:30][C:29]=2[O:28]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 944261-PiperonylpiperazineHCID 18472214(E)-N-[4-(chloromethyl)phenyl]3-(4-methylphenyl)cinnamamide

Product 1

HCID 18472301(E)-N-[4-[1-(3,4-methylenedioxybenzyl)-4-piperazinylmethyl]phenyl]-3-(4-methylphenyl)cinnamamideYield 88.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In DMF (3 ml) was dissolved (E)-N-[4-(chloromethyl)phenyl]-3-(4-methylphenyl)cinnamamide (200 mg), and to the solution were added 1-(3,4-methylenedioxybenzyl)piperazine (158 mg) and potassium carbonate (382 mg). The mixture was stirred at room temperature for 16 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 sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-diisopropylether to give (E)-N-[4-[1-(3,4-methylenedioxybenzyl)-4-piperazinylmethyl]phenyl]-3-(4-methylphenyl)cinnamamide (Compound 57) (266 mg) as colorless crystals.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-diisopropylether

Sources & evidence

ORD record
ord-ad6e8c26634a4e888c460bfad9af3b81
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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