Dimethyl oxalate → methyl N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)oxamate

HRID 1885685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1885685
[NH2:1][CH:2]1[CH2:7][C:6]([CH3:9])([CH3:8])[N:5]([O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:4]([CH3:18])([CH3:17])[CH2:3]1.[C:19](OC)(=[O:24])[C:20]([O:22][CH3:23])=[O:21]>C1(C)C=CC=CC=1>[CH:11]1([O:10][N:5]2[C:6]([CH3:8])([CH3:9])[CH2:7][CH:2]([NH:1][C:19](=[O:24])[C:20]([O:22][CH3:23])=[O:21])[CH2:3][C:4]2([CH3:18])[CH3:17])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1

Komponenten

4

Edukt 2

HCID 11120Dimethyl oxalateHCID 222779844-Amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine

Produkt 1

HCID 23372095methyl N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)oxamateAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 10.0 grams (39.3 mmol) of 4-amino-1-cyclohexyloxy-2,2,6,6-tetramethylpiperidine, 27.8 grams (236 mmol) of dimethyl oxalate and 100 ml of toluene is heated at reflux. Methanol and toluene are removed from the reaction mixture by fractional distillation. The reaction is then filtered and the filtrate is concentrated to obtain a solid. Fractional crystallization of the solid from 9:1 isopropanol:methylene chloride followed by recrystallization from heptane affords 6.5 grams (48% yield) of the title compound as a white solid melting at 124°-126° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureat reflux
  3. customMethanol and toluene are removed from the reaction mixture by fractional distillation
  4. filtrationThe reaction is then filtered
  5. concentrationthe filtrate is concentrated
  6. customto obtain a solid
  7. customFractional crystallization of the solid from 9:1 isopropanol
  8. custommethylene chloride followed by recrystallization from heptane

Quellen und Nachweise

ORD-Eintrag
ord-b3675c1520a24a329d679d62e72f06e0
Quelldatensatz
uspto-grants-1992_09
Patentnummer
US05145893

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