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

HRID 565904Notes

Reaction equation

HRID 565904 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 (3ml) was dissolved (E)-N-[4-(chloromethyl)-phenyl]-3-(4-methylphenyl)cinnamamide (200mg), and to the solution were added 2-(3,4-dimethoxyphenyl)ethylmethyl-amine (132 μl) and potassium carbonate (382mg). The mixture was stirred at room temperature for 12 hours, and to the mixture was added water (50ml). 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 (50ml), and to the mixture was added 4 N hydrochloric acid ethyl acetate solution (0.5ml). The resulting precipitate was filtered and recrystallized from ethyl acetate-methanol to give (E)-N-[4-[N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methyl-aminomethyl]phenyl]-3-(4-methylphenyl)cinnamamide hydrochloride (Compound 63) (245mg) 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 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-fad2b54f5dab42c8ad1b5d948fe829b6
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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