Piperazine → 1-(2,3-Dihydro-benzofuran-2-ylmethyl)-piperazine

HRID 1772218Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1772218
I[CH2:2][CH:3]1[CH2:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[O:4]1.C(=O)([O-])[O-].[K+].[K+].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C(#N)C>[O:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[CH2:7][CH:3]1[CH2:2][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1

Komponenten

5

Edukt 3

HCID 4837PiperazineHCID 11430Potassium CarbonateHCID 3255132-(Iodomethyl)-2,3-dihydro-1-benzofuran

Produkt 1

HCID 31596641-(2,3-Dihydro-benzofuran-2-ylmethyl)-piperazineAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 2-(iodomethyl)-2,3-dihydro-1-benzofuran (5.3 g, 20.4 mmol) in acetonitrile (70 ml) was added potassium carbonate (5.6 g, 40.5 mmol, 2 eq) and piperazine (8.8 g, 102.2 mmol, 5 eq). The resulting mixture was heated at reflux for 2 hours. The solids were then filtered off and the filtrate was concentrated under vacuum. The crude material was purified by silica gel chromatography using 0.5-2.5% methanol in dichloromethane to elute. The product-containing fractions were combined and concentrated under vacuum to afford 1-(2,3-dihydro-1-benzofuran-2-ylmethyl)piperazine as brown oil (2.4 g, 54%); (ES, m/z): [M+H]+ 219; 1H NMR (300 MHz, CDCl3): δ 7.07-7.17 (m, 2H), 6.78-6.85 (m, 2H), 4.92-5.01 (m, 1H), 3.22 (dd, J=9.0 Hz, 15.6 Hz, 1H), 2.91-2.99 (m, 4H), 2.71-2.82 (m, 1H), 2.53-2.71 (m, 6H).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationThe solids were then filtered off
  4. concentrationthe filtrate was concentrated under vacuum
  5. customThe crude material was purified by silica gel chromatography
  6. washto elute
  7. concentrationconcentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f5d1171d16f7463c968d1fad145c89e9
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09249102B2

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