Toluene → 1-[2-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)ethyl]-4-(2-hydroxyethyl)piperazine

HRID 568738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 568738
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.[CH3:10][O:11][C:12]1[C:13]([CH3:38])=[C:14]([CH3:37])[C:15]2[O:20][C:19]([CH2:22][CH2:23]OS(C3C=CC(C)=CC=3)(=O)=O)([CH3:21])[CH2:18][CH2:17][C:16]=2[C:35]=1[CH3:36].C1(C)C=CC=CC=1>O>[CH3:10][O:11][C:12]1[C:13]([CH3:38])=[C:14]([CH3:37])[C:15]2[O:20][C:19]([CH2:22][CH2:23][N:7]3[CH2:8][CH2:9][N:4]([CH2:3][CH2:2][OH:1])[CH2:5][CH2:6]3)([CH3:21])[CH2:18][CH2:17][C:16]=2[C:35]=1[CH3:36]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 76771-(2-Hydroxyethyl)piperazineHCID 139094223,4-dihydro-6-methoxy-2-[2-(p-toluenesulfonyloxy)ethyl]-2,5,7,8-tetramethyl-2H-benzopyran

Produkt 1

HCID 143926471-[2-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)ethyl]-4-(2-hydroxyethyl)piperazineAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution composed of 20 g of N-(2-hydroxyethyl)piperazine, 5 g of 3,4-dihydro-6-methoxy-2-[2-(p-toluenesulfonyloxy)ethyl]-2,5,7,8-tetramethyl-2H-benzopyran and 100 ml of toluene was refluxed for 8 hours in a nitrogen atmosphere. After cooling to room temperature, the reaction mixture was poured into water and extracted with diethyl ether. The extract was washed with water and dried over anhydrous sodium sulfate. Low-boiling substances were distilled off under reduced pressure and the residue was purified by silica gel column chromatography to give 3.66 g of 1-[2-(3,4-dihydro-6-methoxy-2,5,7,8-tetramethyl-2H-benzopyran-2-yl)ethyl]-4-(2-hydroxyethyl)piperazine [Compound (35)] having the following physical characteristics.

Aufarbeitung

  1. temperaturewas refluxed for 8 hours in a nitrogen atmosphere
  2. extractionextracted with diethyl ether
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationwere distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-95ed2f7a1c6443619a465fa4562f040c
Quelldatensatz
uspto-grants-1988_03
Patentnummer
US04728650

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