Triphenylphosphine → 1-(Methylsulfonyl)-4-[4-(trimethylsilylethynyl)phenyl]piperazine

HRID 859925Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 859925
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14](Br)=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3].[CH3:18][Si:19]([C:22]#[CH:23])([CH3:21])[CH3:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>N1CCCCC1.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([C:23]#[C:22][Si:19]([CH3:21])([CH3:20])[CH3:18])=[CH:13][CH:12]=2)[CH2:7][CH2:6]1)(=[O:4])=[O:3]

Komponenten

7

Edukt 3

HCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 219193841-(4-Bromophenyl)-4-(methylsulfonyl)piperazine

Produkt 1

HCID 696067501-(Methylsulfonyl)-4-[4-(trimethylsilylethynyl)phenyl]piperazine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8082PiperidineLösungsmittel

Reaktionsbedingungen

Temperatur
105 °C

Versuchsvorschrift

To a stirred suspension of 1-(methylsulfonyl)-4-(4-bromophenyl)piperazine (4.79 g, 15 mmol, prepared as in example 3), trimethylsilylacetylene (4.15 mL, 30 mmol), Copper (I) iodide (31 mg, 0.17 mmol) and triphenylphosphine (80 mg, 0.3 mmol) in piperidine (60 mL) at 20° C. was added dichlorobis(triphenylphosphine)palladium(II) (31 mg, 45 μmol). The reaction was warmed to 105° C. and stirred for 8 hours under an inert atmosphere. After cooling, the suspension was filtered and washed with toluene. The solid was dissolved in CH2Cl2, washed with water and filtered through silica, washing with CH2Cl2. The filtrate was concentrated and the resulting suspension filtered, washing well with CH2Cl2/iHexane to give 1-(methylsulfonyl)-4-[4-(trimethylsilylethynyl)phenyl]piperazine as a white powder (3.05 g, 9.06 mmol, 60

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe suspension was filtered
  3. washwashed with toluene
  4. dissolutionThe solid was dissolved in CH2Cl2
  5. washwashed with water
  6. filtrationfiltered through silica
  7. washwashing with CH2Cl2
  8. concentrationThe filtrate was concentrated
  9. filtrationthe resulting suspension filtered
  10. washwashing well with CH2Cl2/iHexane

Quellen und Nachweise

ORD-Eintrag
ord-ab3e761a5704466c90be9df35e415438
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153857B2

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