Benzyl chloroformate → 1-Benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylate

HRID 473816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 473816
[C:1]1([CH:7]2[NH:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].C(N(C(C)C)CC)(C)C>O1CCOCC1.C(OCC)(=O)C>[C:1]1([CH:7]2[CH2:8][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:10][CH2:11][N:12]2[C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 2735358Tert-butyl 3-phenylpiperazine-1-carboxylate

Produkt 1

HCID 675145701-Benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylateAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

A solution of tert-butyl 3-phenylpiperazine-1-carboxylate (0.95 g, 3.6 mmol), benzyl chloroformate (0.85 g, 5.0 mmol) and diisopropylethylamine (1.0 g, 7.7 mmol) in dioxane (20 mL) was heated to 95° C. for 3 hours. After cooling, the reaction mixture was diluted with ethyl acetate (100 mL), and washed with saturated aqueous sodium bicarbonate (50 mL) and brine (25 mL). After drying over anhydrous sodium sulfate, filtration and concentration, the residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8) to give 1-benzyl 4-tert-butyl 2-phenylpiperazine-1,4-dicarboxylate (0.84 g, 59% yield).

Aufarbeitung

  1. temperatureAfter cooling
  2. washwashed with saturated aqueous sodium bicarbonate (50 mL) and brine (25 mL)
  3. dry with materialAfter drying over anhydrous sodium sulfate, filtration and concentration
  4. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexanes, 1:8)

Quellen und Nachweise

ORD-Eintrag
ord-80e881508e534ff1bce91a395aef24fb
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637499B2

Notizen zur Reaktion

Wird geladen…