Acetonitrile → 5-Aziridin-1-yl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-yhnethyl)-benzamide

HRID 1532324Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1532324
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([NH:22][CH2:23][CH2:24]Cl)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].C(#N)C>O>[N:22]1([C:19]2[CH:20]=[CH:21][C:2]([Cl:1])=[C:3]([CH:18]=2)[C:4]([NH:6][CH2:7][C:8]23[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]4)[CH2:9]2)[CH2:15]3)=[O:5])[CH2:23][CH2:24]1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 10796Cesium carbonateHCID 114176532-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

Produkt 1

HCID 206700525-Aziridin-1-yl-2-chloro-N-(tricyclo[3.3.1.13,7]dec-1-yhnethyl)-benzamideAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

2-Chloro-5-(2-chloroethyl)amino-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.15 g), cesium carbonate (0.192 g) and acetonitrile (3 ml) were combined and heated in a sealed tube at 100° C. for 24 hours. The cooled reaction mixture was poured into water (50 ml) and the product extracted into ethyl acetate, dried over magnesium sulphate, filtered and concentrated under reduced pressure. The crude product was purified by NPHPLC eluting with 0-5% ethanol in dichloromethane to give the title compound as a white solid (0.023 g).

Aufarbeitung

  1. customThe cooled reaction mixture
  2. extractionthe product extracted into ethyl acetate
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by NPHPLC
  7. washeluting with 0-5% ethanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-6edbd64372434046b8f795b328408452
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06201024B1

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