N-Methylcyclohexylamine → 4-[[(N-cyclohexyl-N-methylamino)methylene]amino]-3-pyridinol

HRID 362196

Reaktionsgleichung

Reaktionsgleichung von HRID 362196
[CH3:1][N:2]([CH:4]=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[CH:8][C:7]=1[OH:12])[CH3:3].CN[CH:15]1[CH2:20][CH2:19]C[CH2:17][CH2:16]1>C1(C)C=CC=CC=1>[CH:3]1([N:2]([CH:4]=[N:5][C:6]2[CH:11]=[CH:10][N:9]=[CH:8][C:7]=2[OH:12])[CH3:1])[CH2:19][CH2:20][CH2:15][CH2:16][CH2:17]1

Komponenten

4

Edukt 2

HCID 7514N-MethylcyclohexylamineHCID 153809294-[[(Dimethylamino)methylene]amino]-3-pyridinol

Produkt 1

HCID 153809374-[[(N-cyclohexyl-N-methylamino)methylene]amino]-3-pyridinolAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-[[(dimethylamino)methylene]amino]-3-pyridinol (5.00 g), N-methylcyclohexylamine (5.20 g), and anhydrous toluene (50 mL) was heated at reflux under nitrogen for 17 hours. The solution was concentrated under reduced pressure and the crude product chromatographed on silica gel (10% methanol in dichloromethane) to afford 5.92 g of solid. Recrystallization from ethyl acetate/hexanes afforded 4.90 g of crystalline material, m.p. 127°-129° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 17 hours
  3. concentrationThe solution was concentrated under reduced pressure
  4. customthe crude product chromatographed on silica gel (10% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-37c99f83914c4ca58690a7333dfd8aca
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05869480

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