Triethylamine → 1-(Methylsulfonyl)-4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine

HRID 1723826

Reaktionsgleichung

Reaktionsgleichung von HRID 1723826
[F:1][C:2]([F:18])([F:17])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>C(Cl)Cl>[CH3:26][S:27]([N:14]1[CH2:15][CH2:16][N:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][C:2]([F:1])([F:17])[F:18])=[CH:10][CH:9]=2)[CH2:12][CH2:13]1)(=[O:29])=[O:28]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 435103441-[4-(2,2,2-Trifluoroethoxy)phenyl]piperazine

Produkt 1

HCID 210686241-(Methylsulfonyl)-4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazineAusbeute 19,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

1-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine (13.48 g, 50 mmol) was dissolved in DCM (500 mL) and cooled to 0° C. Triethylamine (29 mL, 0.2 mol) was added, followed by the dropwise addition of methanesulfonyl chloride (4.2 mL, 55 mmol). The reaction was then allowed to warm to room temperature and stir overnight, before being quenched by the addition of water. The layers were separated, and the organic phase dried (MgSO4), filtered and concentrated. The residue was recrystallised from hot ethanol to give pure 1-(methylsulfonyl)-4-[4-(2,2,2-trifluoroethoxy)phenyl]piperazine (3.3 g, 18%).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. custombefore being quenched by the addition of water
  3. customThe layers were separated
  4. dry with materialthe organic phase dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallised from hot ethanol

Quellen und Nachweise

ORD-Eintrag
ord-0c7223e91e814e678a6c46b4b906b5a2
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07485644B2

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