Triethylamine → 7-(3-Cyanobenzamido)-1-(4-methyl-1-piperazinyl)-naphthalene

HRID 235115Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 235115
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:26]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32])#[N:27]>C(#N)C>[C:26]([C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31]([NH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[N:12]2[CH2:17][CH2:16][N:15]([CH3:18])[CH2:14][CH2:13]2)=[CH:4][CH:3]=1)=[O:32])#[N:27]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3084833-Cyanobenzoyl chlorideHCID 233534847-Amino-1-(4-methyl-1-piperazinyl)-naphthalene

Produkt 1

HCID 223693767-(3-Cyanobenzamido)-1-(4-methyl-1-piperazinyl)-naphthaleneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

The title product was prepared following the procedure of example 3 from 7-amino-1-(4-methyl-1-piperazinyl)-naphthalene (0.213 g, 0.883 mmol) and triethylamine (0.258 mL, 1.94 mmol) and 3-cyanobenzoyl chloride (0.322 g, 1.94 mmol) in acetonitrile (10 mL) with stirring at reflux for 2 hours and then at room temperature overnight. The mixture was concentrated and the residue was taken up in methylene chloride. This organic solution was washed with 0.5N sodium hydroxide, dried over calcium sulfate and concentrated. The product was isolated by silica gel flash chromatography and recrystallization from isopropyl alcohol to yield 0.184 g of (60%) of the title compound: mp 220°-222° C. Analysis calculated for C23H22N4O: C, 74.57; H, 5.99; N, 15.12. Found: C, 74.42; H, 5.78; N, 14.96.

Aufarbeitung

  1. customThe title product was prepared
  2. temperatureat reflux for 2 hours
  3. customat room temperature
  4. customovernight
  5. concentrationThe mixture was concentrated
  6. washThis organic solution was washed with 0.5N sodium hydroxide
  7. dry with materialdried over calcium sulfate
  8. concentrationconcentrated
  9. customThe product was isolated by silica gel flash chromatography and recrystallization from isopropyl alcohol

Quellen und Nachweise

ORD-Eintrag
ord-d17dbf537ab94c9fbc1bc72d2628404f
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597826

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