Di-p-tolylcarbodiimide → benzoic acid 1-(N,N'-di-p-tolyl-carbamimidoyloxy)-2,2,6,6-tetramethyl-piperidin-4-yl ester

HRID 1184985Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1184985
[OH:1][N:2]1[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:4][C:3]1([CH3:20])[CH3:19].[C:21]1([CH3:37])[CH:26]=[CH:25][C:24]([N:27]=[C:28]=[N:29][C:30]2[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=2)=[CH:23][CH:22]=1>C1COCC1>[C:33]1([CH3:36])[CH:34]=[CH:35][C:30]([NH:29][C:28]([O:1][N:2]2[C:7]([CH3:9])([CH3:8])[CH2:6][CH:5]([O:10][C:11](=[O:18])[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:4][C:3]2([CH3:20])[CH3:19])=[N:27][C:24]2[CH:23]=[CH:22][C:21]([CH3:37])=[CH:26][CH:25]=2)=[CH:31][CH:32]=1

Komponenten

4

Edukt 2

HCID 69763Di-p-tolylcarbodiimideHCID 6881781-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine

Produkt 1

HCID 58526176benzoic acid 1-(N,N'-di-p-tolyl-carbamimidoyloxy)-2,2,6,6-tetramethyl-piperidin-4-yl esterAusbeute 63,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1-Hydroxy-4-benzoyloxy-2,2,6,6-tetramethylpiperidine (5.75 g, 20.7 mmol) [prepared as described in Example 6] and di-p-tolylcarbodiimide (4.8 g, 21.6 mmol) are dissolved in THF (40 ml) and the solution is stirred at room temperature for 17 hours. The solvent is evaporated and the residue is chromatographed on silica gel with hexane-ethyl acetate (9:1). The pure fractions are recrystallized from acetonitrile to afford 6.55 g of the title compound as a colorless solid, mp. 124-128° C.

Aufarbeitung

  1. customThe solvent is evaporated
  2. customthe residue is chromatographed on silica gel with hexane-ethyl acetate (9:1)
  3. customThe pure fractions are recrystallized from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-62e733b4542c43f492c9e657139f208b
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08669398B2

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