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

HRID 1277080
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HRID 1277080 반응식
[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]
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참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-db1d224bdb9745c588012b68b422b9b8
출처 데이터셋
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06166006

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