Water → N-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide

HRID 1282050Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1282050
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[C:14]1([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:14]1([N:20]2[CH2:25][CH2:24][N:23]([CH2:2][C:3]3[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=3)[CH2:22][CH2:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 70961-PhenylpiperazineHCID 11430Potassium CarbonateHCID 15550682N-((4-(chloromethyl)phenyl)methyl)acetamide

Produkt 1

HCID 11652722N-(4-((4-Phenylpiperazin-1-yl)methyl)phenylmethyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of N-(4-chloromethylphenylmethyl)acetamide (1.65 g), 1-phenylpiperazine (1.3 ml) and potassium carbonate (1.2 g) in dimethylformamide (50 ml) was stirred at 60° C. for 1 hr. The reaction mixture was poured into water (200 ml) and extracted with ethyl acetate (100 ml×3). The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a brown solid (4.4 g). The obtained solid was purified by silica gel column chromatography (developing solvent; chloroform:methanol=10:1) to give a pale-brown solid (3.45 g). The obtained solid was crystallized from ethyl acetate and the crystals were recrystallized from a mixture of ethyl acetate, ethanol and hexane to give the title compound (1.4 g) as white crystals, m.p.=135-136° C.

Aufarbeitung

  1. extractionextracted with ethyl acetate (100 ml×3)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ee6af7af31e64e539d3522ada6101cb2
Quelldatensatz
uspto-grants-2002_09
Patentnummer
US06455528B1

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