2-Pyridinecarboxaldehyde → 1-(pyridin-2-yl)-N-((1R,2R)-2-(((pyridin-2-yl)methylidene)amino)cyclohexyl)methanimine

HRID 857829Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 857829
[NH2:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:8].[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=O>CO>[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[N:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C@H:3]1[N:8]=[CH:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=1

Komponenten

4

Edukt 2

HCID 142732-PyridinecarboxaldehydeHCID 438061,2-Diaminocyclohexane, trans-

Produkt 1

HCID 100629331-(pyridin-2-yl)-N-((1R,2R)-2-(((pyridin-2-yl)methylidene)amino)cyclohexyl)methanimine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

15.0 g (0.13 mol) of trans-1,2-diaminocyclohexane are dissolved in 80 ml of methanol and, at room temperature, 28.1 g (0.26 mol) of pyridine-2-aldehyde are added a little at a time. The solution is refluxed for one hour and then cooled to room temperature. The precipitated solid is filtered off and dried in an oil pump vacuum. The product is obtained in the form of a light-yellow powder in a yield of 23 g (79 mmol, 60%). 1H-NMR (400 MHz, CDCl3): δ=8.55 (m, 2H, Py), 8.31 (s, 2H, ═C—H), 7.88, 7.63, 7.21 (3×m, 6H, Py), 3.52 (m, 2H, NC—H), 1.90–1.49 (m, 8H, (CH2)4) ppm.

Aufarbeitung

  1. temperatureThe solution is refluxed for one hour
  2. filtrationThe precipitated solid is filtered off
  3. customdried in an oil pump vacuum
  4. customThe product is obtained in the form of a light-yellow powder in a yield of 23 g (79 mmol, 60%)

Quellen und Nachweise

ORD-Eintrag
ord-9a344a5e80f2460db85d783760a81afd
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148174B2

Notizen zur Reaktion

Wird geladen…