Potassium Carbonate → (E)-N-[4-[N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminomethyl]phenyl]-3-(4-methylphenyl)cinnamamide hydrochloride

HRID 2228101Notes

Reaction equation

HRID 2228101 reaction equation
[Cl:1][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.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH2:37][CH2:38][NH:39][CH3:40])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36].C(=O)([O-])[O-].[K+].[K+].C(OC(=O)C)C.Cl>CN(C=O)C.C(OCC)(=O)C.O>[ClH:1].[CH3:27][O:28][C:29]1[CH:30]=[C:31]([CH2:37][CH2:38][N:39]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:26])/[CH:11]=[CH:12]/[C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([C:19]4[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=4)[CH:14]=3)=[CH:5][CH:4]=2)[CH3:40])[CH:32]=[CH:33][C:34]=1[O:35][CH3:36]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 77039N-MethylhomoveratrylamineHCID 18472214(E)-N-[4-(chloromethyl)phenyl]3-(4-methylphenyl)cinnamamideHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 18472486(E)-N-[4-[N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylaminomethyl]phenyl]-3-(4-methylphenyl)cinnamamide hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

In DMF (3 ml) was dissolved (E)-N-[4—(chloromethyl)phenyl]-3—(4-methylphenyl)cinnamamide (200 mg), and to the solution were added 2—(3,4-dimethoxyphenyl)ethylmethylamine (132 μl) and potassium carbonate (382 mg). The mixture was stirred at room temperature for 12 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 separated and purified with column chromatography (ethyl acetate) to give colorless amorphous, which was dissolved in ethyl acetate (50 ml), and to the mixture was added 4N hydrochloric acid ethyl acetate solution (0.5 ml). The resulting precipitate was filtered and recrystallized from ethyl acetate-methanol to give (E)-N-[4-[N-[2—(3,4-dimethoxyphenyl)ethyl]-N-methylaminomethyl]phenyl]-3—(4-methylphenyl)cinnamamide hydrochloride (Compound 63) (245 mg) as colorless crystals.

Workup

  1. extractionThe mixture was extracted with ethyl
  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 separated
  6. custompurified with column chromatography (ethyl acetate)
  7. customto give colorless amorphous, which
  8. filtrationThe resulting precipitate was filtered
  9. customrecrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-38448d8a6c014b138be8f6236531441c
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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