6-Nitroveratraldehyde → 6-Nitroveratrylidene-2-aminomethyltetrahydropyran

HRID 597507Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 597507
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][O:4]1.[N+:9]([C:12]1[C:17]([CH:18]=O)=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)([O-:11])=[O:10]>C(O)C>[N+:9]([C:12]1[C:17]([CH:18]=[C:8]2[CH2:7][CH2:6][CH2:5][O:4][CH:3]2[CH2:2][NH2:1])=[CH:16][C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=1)([O-:11])=[O:10]

Komponenten

4

Edukt 2

HCID 885056-NitroveratraldehydeHCID 97924(Tetrahydro-2H-pyran-2-ylmethyl)amine

Produkt 1

HCID 542260806-Nitroveratrylidene-2-aminomethyltetrahydropyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel2×

Versuchsvorschrift

A solution of 2-aminomethyltetrahydropyran (51 g, 0.44 mole) and ethanol (50 ml) was slowly added to a heated suspension of 6-nitroveratraldehyde (84 g, 0.4 mole) and ethanol (600 ml). The resulting solution was refluxed for 1.5 hrs and cooled overnight. The solution was concentrated to dryness and the oil was dissolved in chloroform and washed with water. The chloroform extract was concentrated leaving a dark oil which crystallized upon standing. The solid was suspended in hexane and filtered (117 g, 95%), m.p. 89°-96°.

Aufarbeitung

  1. temperatureThe resulting solution was refluxed for 1.5 hrs
  2. temperaturecooled overnight
  3. concentrationThe solution was concentrated to dryness
  4. dissolutionthe oil was dissolved in chloroform
  5. washwashed with water
  6. extractionThe chloroform extract
  7. concentrationwas concentrated
  8. customleaving a dark oil which
  9. customcrystallized
  10. filtrationfiltered (117 g, 95%), m.p. 89°-96°

Quellen und Nachweise

ORD-Eintrag
ord-1bd9fd7b3aab4196b6a24a985206c08b
Quelldatensatz
uspto-grants-1977_03
Patentnummer
US04014886

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