Methyl Isobutyl Ketone → 4-[4-[2-(Indan-2-yl)ethyl]piperazin-1-yl]-1H-indole

HRID 1385077Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1385077
[N:1]1([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.I[CH2:17][CH2:18][CH:19]1[CH2:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH2:20]1.C(C(C)=O)C(C)C>CN1CCCC1=O>[CH2:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:27][CH:19]1[CH2:18][CH2:17][N:4]1[CH2:3][CH2:2][N:1]([C:7]2[CH:15]=[CH:14][CH:13]=[C:12]3[C:8]=2[CH:9]=[CH:10][NH:11]3)[CH2:6][CH2:5]1

Komponenten

5

Edukt 3

HCID 7909Methyl Isobutyl KetoneHCID 5945904-(piperazin-1-yl)-1H-indoleHCID 185458332-(2-Iodoethyl)indane

Produkt 1

HCID 185459054-[4-[2-(Indan-2-yl)ethyl]piperazin-1-yl]-1H-indoleAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

A mixture of 4-(piperazin-1-yl)-1H-indole (1.5 g), 2-(2-iodoethyl)indane (2.0 g), K2C(3, methyl isobutyl ketone (150 ml), and N-methylpyrrolidone (10 ml ) was boiled under reflux for 3 h. The mixture was allowed to cool to room temperature, filtered, and concentrated in vacuo. The residue was purified on silica gel eluted with ethyl acetate-heptane (1:2) to give a crystalline compound, which was recrystallized (ethyl acetate) to give the title compound (1.2 g, 47%). Mp 146-147° C. 1H NMR (CDCl3) δ 1.70-1.85 (m, 2H), 2.40-2.70 (m, 5H), 2.75 (broad s, 4H), 3.00-3.15 (m, 2H), 3.30 (broad s, 4H), 6.55 (s, 1H), 6.60 (d, 1H), 7.00-7.30 (m, 711), 8.20 (broad s, 1H). MS m/z (%): 346 (MH+, 34%), 159 (88%), 145 (100%).

Aufarbeitung

  1. temperatureunder reflux for 3 h
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified on silica gel
  5. washeluted with ethyl acetate-heptane (1:2)
  6. customto give a crystalline compound, which
  7. customwas recrystallized (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-7fc71042bab3452cba683d7353ab5509
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06262087B1

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