Diisopropylethylamine → 1-(Pent-4-ynyl)-4-(pyridin-2-yl)piperazine

HRID 1984098Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984098
CS(O[CH2:6][CH2:7][CH2:8][C:9]#[CH:10])(=O)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(N(C(C)C)CC)(C)C>C1COCC1>[CH2:6]([N:20]1[CH2:21][CH2:22][N:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][N:11]=2)[CH2:18][CH2:19]1)[CH2:7][CH2:8][C:9]#[CH:10]

Komponenten

5

Edukt 3

HCID 81531DiisopropylethylamineHCID 944591-(2-Pyridyl)piperazineHCID 12476209Pent-4-yn-1-yl methanesulfonate

Produkt 1

HCID 866082261-(Pent-4-ynyl)-4-(pyridin-2-yl)piperazineAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of pent-4-ynyl methanesulfonate (1.05 g), 1-(pyridin-2-yl)piperazine (1.02 g) and diisoproylethylamine (1.2 mL) in THF (5 mL) was heated to reflux overnight. The mixture was concentrated, diluted with aq. NaOH 2M (10 mL) and extracted with DCM (2×50 mL). Drying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0) afforded 1-(pent-4-ynyl)-4-(pyridin-2-yl)piperazine (1.02 g).

Aufarbeitung

  1. temperatureto reflux overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with aq. NaOH 2M (10 mL)
  4. extractionextracted with DCM (2×50 mL)
  5. dry with materialDrying (Na2SO4) and silica gel flash chromatography (EtOAc/hexane 2:1→2:0)

Quellen und Nachweise

ORD-Eintrag
ord-f5871390d0b24938bc871753e3cf0295
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544672B2

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