n-Butyl-2,2,6,6-tetramethyl-4-piperidinamine → Ethyl N-[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-1,3,5-triazin-6-yl]glycinate

HRID 375773

Reaktionsgleichung

Reaktionsgleichung von HRID 375773
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:3]=1.[CH3:16][C:17]1([CH3:30])[CH2:22][CH:21]([NH:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:20][C:19]([CH3:29])([CH3:28])[NH:18]1.C(=O)(O)[O-].[Na+]>C1(C)C(C)=CC=CC=1>[CH2:24]([N:23]([C:2]1[N:7]=[C:6]([N:23]([CH:21]2[CH2:22][C:17]([CH3:30])([CH3:16])[NH:18][C:19]([CH3:28])([CH3:29])[CH2:20]2)[CH2:24][CH2:25][CH2:26][CH3:27])[N:5]=[C:4]([NH:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:3]=1)[CH:21]1[CH2:20][C:19]([CH3:29])([CH3:28])[NH:18][C:17]([CH3:30])([CH3:16])[CH2:22]1)[CH2:25][CH2:26][CH3:27]

Komponenten

5

Edukt 3

HCID 118285n-Butyl-2,2,6,6-tetramethyl-4-piperidinamineHCID 516892Sodium BicarbonateHCID 147462614,6-dichloro-2-ethoxycarbonylmethylamino-S-triazine

Produkt 1

HCID 14746206Ethyl N-[2,4-bis(N-butyl-N-(2,2,6,6-tetramethyl-4-piperidyl)amino)-1,3,5-triazin-6-yl]glycinateAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Versuchsvorschrift

2.36 g of ethyl N-(2,4-dichloro-1,3,5-triazin-6-yl)glycinate [obtained as described in Preparation 4(A)], 4.19 g of 2,2,6,6-tetramethyl-4-(butylamino)piperidine [obtained as described in Preparation i(A)] and 2.77 g of sodium bicarbonate were heated under reflux in 20 ml of xylene for 29 hours. At the end of this time, the xylene was removed by distillation under reduced pressure, and a mixture of methylene chloride and water was added to the resulting residue, after which the mixture was shaken. The methylene chloride layer was separated, dried and concentrated by evaporation under reduced pressure, and the resulting residue was purified by silica gel column chromatography (using a 20:10:1:1 by volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent), to yield 5.46 g of the title compound melting at 40° C.

Aufarbeitung

  1. customAt the end of this time, the xylene was removed by distillation under reduced pressure
  2. additiona mixture of methylene chloride and water
  3. additionwas added to the resulting residue
  4. customThe methylene chloride layer was separated
  5. customdried
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography (
  8. additionby volume mixture of hexane, diethyl ether, ethanol and triethylamine as eluent),

Quellen und Nachweise

ORD-Eintrag
ord-4b2376a98a4048179b6e95cb7445ec51
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486556

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