Water → Depyrazine 7,8-Dinitrophenyl Varenicline

HRID 2182779Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2182779
[N+:1]([C:4]1[C:14]([N+:15]([O-:17])=[O:16])=[CH:13][C:12]2[CH:11]3[CH2:18][CH:7]([CH2:8][N:9](C(=O)C(F)(F)F)[CH2:10]3)[C:6]=2[CH:5]=1)([O-:3])=[O:2].C([O-])([O-])=O.[Na+].[Na+].O>CO>[N+:15]([C:14]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]2[CH:7]3[CH2:18][CH:11]([CH2:10][NH:9][CH2:8]3)[C:12]=2[CH:13]=1)([O-:17])=[O:16]

Komponenten

5

Edukt 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 218647441-(7,8-Dinitro-1,2,4,5-tetrahydro-3H-1,5-methano-3-benzazepin-3-yl)-2,2,2-trifluoroethan-1-one

Produkt 1

HCID 9878181Depyrazine 7,8-Dinitrophenyl VareniclineAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-(4,5-Dinitro-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-10-yl)-2,2,2-trifluoro-ethanone (3.7 g, 10.7 mmol) and Na2CO3 (2.3 g, 21.4 mmol) were combined in MeOH (50 mL) and H2O (20 mL) then warmed to reflux for 18 hours. The reaction was cooled, concentrated, treated with H2O and extracted with CH2Cl2 (3×50 mL) then dried through a cotton plug. After concentration, the residue was chromatographed to provide brown solids (1.9 g, 71%) (TLC 5% MeOH/CH2Cl2 (NH3) Rf 0.36). 1H NMR (400 MHz, CDCl3) δ 7.69 (s, 2H), 3.17 (br s, 2H), 3.11 (d, J=12.6 Hz, 2H), 2.53 (m, 1H), 2.07 (d, J=11.0 Hz, 1H). GCMS m/e 249 (M+).

Aufarbeitung

  1. temperatureto reflux for 18 hours
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated
  4. additiontreated with H2O
  5. extractionextracted with CH2Cl2 (3×50 mL)
  6. customthen dried through a cotton plug
  7. concentrationAfter concentration
  8. customthe residue was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-b6c6cc73f2f4492097aee5c13b96c12b
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06897310B2

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