Acetic Acid → 2-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl acetate

HRID 1038512Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038512
[F:1][C:2]([F:28])([F:27])[C:3]([C:9]1[CH:10]=[N:11][C:12]([N:18]2[CH2:23][CH2:22][N:21]([CH2:24][CH2:25][OH:26])[CH2:20][CH2:19]2)=[CH:13][C:14]=1[CH2:15][CH2:16][CH3:17])([OH:8])[C:4]([F:7])([F:6])[F:5].N1C=CC=CC=1.[C:35](O)(=[O:37])[CH3:36].CO>ClCCl>[C:35]([O:26][CH2:25][CH2:24][N:21]1[CH2:22][CH2:23][N:18]([C:12]2[CH:13]=[C:14]([CH2:15][CH2:16][CH3:17])[C:9]([C:3]([OH:8])([C:4]([F:7])([F:6])[F:5])[C:2]([F:27])([F:1])[F:28])=[CH:10][N:11]=2)[CH2:19][CH2:20]1)(=[O:37])[CH3:36]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 887MethanolHCID 1049PyridineHCID 866471781,1,1,3,3,3-Hexafluoro-2-{6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-propylpyridin-3-yl}propan-2-ol

Produkt 1

HCID 866471772-{4-[5-(1,1,1,3,3,3-Hexafluoro-2-hydroxypropan-2-yl)-4-propylpyridin-2-yl]piperazin-1-yl}ethyl acetateAusbeute 36 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1,1,1,3,3,3-Hexafluoro-2-{6-[4-(2-hydroxyethyl)piperazin-1-yl]-4-propylpyridin-3-yl}propan-2-ol (208 mg, 0.501 mol) was dissolved in dichloromethane (2.5 mL), added pyridine (121 μL, 1.50 mmol) and anhydrous acetic acid (142 μL, 1.50 mmol) under ice-cold conditions, and the mixture was stirred at room temperature for 3 hours. The reaction solution was added methanol, stirred at room temperature for 0.5 hours. The reaction solution was concentrated in vacuo, extracted with chloroform. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The title compound (247 mg) was obtained as a red-brown oil.

Aufarbeitung

  1. stirringstirred at room temperature for 0.5 hours
  2. concentrationThe reaction solution was concentrated in vacuo
  3. extractionextracted with chloroform
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dab76b4c5c5d4da2b96dd1aed965a859
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551985B2

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